My PayPal shutdown story

One of my favorite travel hacking techniques, and one which I've written about repeatedly in the past, relies on a unique feature of the online payments processor PayPal: it's the only product I'm aware of that allows you to earn miles and points when loading your account (by purchasing a PayPal Cash reload card using a rewards-earning credit card), and also when unloading your account (by earning 1% cash back using a PayPal Debit MasterCard).

Now that there are broad reports of Vanilla Reload Network reload cards no longer being sold via credit card at 7-11 store locations, this technique has become even more valuable. By purchasing PayPal Cash cards at a 7-11 location that posts as bonused "gas station" spend, you can earn double Chase Ultimate Rewards points or US Bank Flexpoints, then earn an additional 1% cash back by using a PayPal Debit MasterCard to load a Visa Buxx card or simply purchase Vanilla Reload Network reload cards at a CVS or other unbonused store location that continues to allow them to be sold. Using this simple technique, I've earned $189 in cash back just since March – and that's in addition to the miles and points I earn from purchasing the PayPal Cash cards.

Unfortunately, the single most important ingredient in this technique is an open PayPal account...and I don't have one anymore. That's right, last week I was completely shut down by PayPal. I want to share some of the things I was doing that did or could have contributed to my shutdown, so you can avoid repeating my mistakes.

1. I used PayPal overseas. This is a weird one, since PayPal has users all over the world. However, this is the very first thing I did that raised red flags with PayPal. They closely track where you typically log into your account from, and if they detect an unusual login they will freeze your account until you prove your identity.
2. I logged into PayPal using Tor. Tor is a web service that allows you to surf the web anonymously.  Since Tor routes your internet traffic all over the world, it's a turbo-charged corollary of the point above: it looks very suspicious to PayPal.
3. I had multiple PayPal accounts.  I've had a PayPal business account for years, since I use to do a fair amount of buying and selling on Ebay. Towards the beginning of this year, when I started using PayPal to travel hack, I decided to see if I could open a new account, which would allow me to double my rolling 30-day PayPal Cash load limit from $4,000 to $8,000. I was able to do so easily, and I "verified" the account by adding a bank account and providing my Social Security number. Once I'd done that, I loaded PayPal Cash cards to my new, personal account and send the money to my business account to be liquidated.
4. I got greedy.  Sometimes, I didn't bother spending the money I'd loaded to my account through PayPal Cash – instead, I withdrew it immediately to my bank account. Now, there's a minor distinction here: I always spent the money I loaded directly to my business account; however when I sent money over from my new, personal account I assumed that the money had been cleared into the system so it was safe for immediate withdrawal.

In retrospect these are all obvious mistakes with simple solutions: when overseas, use a VPN so you always appear to be located in the US; never login to PayPal while using Tor; stick to one PayPal account; and always spend your PayPal Cash loads – never withdraw them directly to your bank account.

Daraius at Million Mile Secrets had a somewhat similar experience, which you can read about here, and the Points Guy got a warning from PayPal after loading and unloading funds using Green Dot MoneyPaks.

I still think this is a great strategy to bring down your cost per dollar of manufactured spend. However, it does take some care to make sure you don't trip over any of PayPal's red lines when it come to fraud and money laundering controls.

Delta devalued their award chart, Alaska didn't

I consider Alaska Airlines Mileage Plan miles to be among the most valuable rewards currencies, since in addition to Alaska's own flights, they can be redeemed on a range of airline partners, including both American Airlines and Delta Airlines. Alaska has access to American's MileSAAver award space and "low-level" Delta award space. You can view all their airline partners here.

Alaska miles just got even more valuable.  On August 14th, Delta announced they were increasing the cost of low-level BusinessElite awards from the United States to Europe, Australia, Asia, South Africa and South America for awards beginning on or after June 1, 2014. Here, Frequent Miler shares his thoughts on "tricking" the devaluation by adding a domestic one-way before June 1.

Alaska's award chart hasn't changed.  It's long been a curious fact about the Mileage Plan program that BusinessElite redemptions on Delta to Europe cost just 90,000 Mileage Plan miles, while the same ticket would cost 100,000 Skymiles. Here's a chart showing the Delta devaluation and the cost of the same flights in Alaska miles:

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Here's a sample flight I found on Delta from Los Angeles to Sydney on June 5, 2014, after the devaluation has gone into effect. You can see the price is showing correctly at 160,000 Skymiles:

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And here's the same flight, on the same day, but booked using Alaska Mileage Plan miles. It costs just 105,000 Mileage Plan miles:

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What does this mean for you? I've long said that if you don't have or want elite status on Delta or American, you should be crediting your flights on those airlines to Alaska. That's now even more true if you plan on using your miles for premium international awards. Additionally, if your paid flights are primarily international, so you don't have to worry about missing domestic upgrades, you may want to think about getting elite status with Alaska, which comes with 50% and 100% bonus miles on paid flights, free checked bags, and other benefits.

Besides flying, you can earn unlimited Alaska miles using the Bank of America Alaska Airlines debit card (I do this – it works), or the Bank of America Alaska Airlines Visa Signature.

Additionally, Mileage Plan is a transfer partner of Starwood Preferred Guest, and you'll earn 25% bonus miles when you transfer 20,000, 40,000, or 60,00 Starpoints into your Mileage Plan account. The Starwood Preferred Guest American Express card currently has a signup bonus of 30,000 Starpoints.

US Bank Kiva loans aren't a hack: they're policy

It's long been an open secret in the travel hacking community that US Bank credit cards which have "charity" as a bonus category also bonus loans make through the micro-lending site Kiva.org. This is one of the first hacks that I took advantage of, since if you're using a US Bank Flexperks Travel Rewards credit card you can earn 3% cash back or 6% back in paid airfare by making Kiva loans. Many of those loans have repayment periods between 4 and 6 months, so if you have cash that you're willing to tie up in these loans, you can earn a decent annualized return, even if you're just redeeming your Flexpoints for cash back, instead of airline tickets.

While I mention this trick in my ebook, The Free-quent Flyer's Manifesto, it's never been entirely clear whether this was an oversight on US Bank's part, a side-effect of their payments being processed by PayPal, or was in fact an intentional policy decision.

I've discovered that rather than an oversight, bonused Kiva loans are an advertised benefit of at least one US Bank credit card program.

As I mentioned last month in my post on product changes, I recently changed one of my two US Bank Flexperks Travel Rewards cards into a US Bank Cash+ card (apply in-branch only, or ask for a product change), which has no annual fee and offers 5% cash back on up to $2,000 in spending per quarter in two categories of your choosing (and 2% cash back in your choice of gas stations, grocery stores, or drug stores).

My US Bank online rewards center has now updated with the Cash+ rewards program, so I decided to check out what the 5% categories were this quarter. "Charity" was among them, as it has been since the card first became available. Unlike with the Flexperks Travel Rewards card, however, the Cash+ rewards center provides a lengthy list of organizations where spending is eligible for 5% cash back. And sure enough, there in the second column is Kiva: 

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Of course, the fact that US Bank advertises Kiva as one eligible merchant that's eligible for the "Charity" category bonus right now doesn't mean they will do so forever, or even that "Charity" will return as a bonus category next quarter, since these categories are regularly changed and reshuffled. However, at this point I think this is the low-hanging fruit of the travel hacking game, and I do strongly recommend at least thinking about getting in on the Charity category bonus with one of those two cards.

Things to keep in mind

Of course, this isn't a risk-free play and it isn't for everybody. Here are some things to keep in mind:

1. Kiva loans are not risk-free. I've never had a default among the approximately $10,000 I've loaned through Kiva, but it certainly happens. The average default rate appears to be about 0.98%.
2. You can minimize, but not eliminate, the risk of default by selecting loans that are offered by partners with a 0% delinquency and default rate, and that have a risk rating of 5 out of 5 stars. This will reduce the number of loans you can consider, however.
3. Kiva deposits and withdrawals are processed by PayPal . That means you need an open PayPal account in order to make Kiva loans. This may not be an option if you've have your accounts closed or if you've been blacklisted by PayPal (more on this coming soon).
4. Deposits to Kiva are instantaneous, withdrawals take 1-2 weeks. This has actually improved considerably: formerly withdrawals could take up to a month to process.
5. US Bank credit cards can be difficult to be approved for. I've always received immediate online approval, but that's not the case for everybody, especially those with lots of recent credit inquiries. One of my most popular blog posts was my step-by-step instructions for one trick you can use to increase your chances of approval for US Bank cards.

Let me know in the comments if you have any more questions on making Kiva loans with US Bank credit cards. 

The best hacks I've missed out on

By now, a lot of people have heard about classic hacks of days gone by, like ordering presidential dollar coins from the US Mint with a rewards-earning credit card, depositing the coins unopened into a bank account, and then paying off the credit card balance. What's often forgotten is the incredible amount of work that went into carrying out this hack: lots of trips to the post office or Mail Boxes Etc.; negotiating with bank managers to accept your coins for deposit; and of course hauling a bunch of heavy coins around town. All to manufacture non-bonused credit card spend! It might have been good work, but it was still work, and it wasn't free.

On the other hand, other hacks really are too good to be true, and these are the ones I really regret not taking advantage of.

Priority Club to Amtrak Transfers

The day before Christmas last year, I woke up to a series of confusing messages about Priority Club and Amtrak. Since Priority Club isn't a program I focus on, I put it on the back burner. Later that afternoon, after lots of trips to the airport picking up family members, I went back and discovered I'd missed out on an incredible deal: the ability to transfer 5,000 Priority Club points into 6,666 Amtrak Guest Rewards points.

Since you can purchase Priority Club points at a cost of 0.7 cents each, this was a chance to buy Amtrak Guest Rewards points at just over half a cent each. Since I value Amtrak Guest Rewards points at between 4 and 6 cents each for Acela First Class tickets and long-haul sleeper accomodations, this was a chance to buy those tickets for pennies on the dollar. Needless to say, I wasn't as merry as I could have been that Chirstmas!

Home Improvement Gift Cards

Last week Frequent Miler gave a great rundown of this short-lived opportunity. Basically, if you were in the right place at the right time, you could purchase – in-person – vast quantities of "Home Improvement Gift Cards," which had begun to be treated as true PIN-based debit cards at merchants like Walmart. The window of opportunity quickly slammed shut, but there was a day or two where points could be purchased for free (if you had load room on your Bluebird or Gobank cards) or for the price of a Walmart money order (around 0.14 cents per dollar of manufactured spend).

Unfortunately, I wasn't in the right place at the right time – they don't sell Home Improvement Gift Cards in Europe! 

Chase Gift Cards

For months now, Chase has been selling gift cards online with no purchase or shipping fees. Best of all, these cards can be configured with PIN codes, which allow them to be used to load Bluebird or Gobank at Walmart, or purchase money orders in many stores that accepts PIN-based debit cards (though USPS code their money orders differently and do not consistently work with all kinds of gift cards).

There are a few limitations on the purchase of these cards: 

1. they can only be purchased using credit cards issued by Chase;
2. each Chase credit card can be used to purchase up to $2,600 per rolling 30-day period;

If this deal's still going on, why have I missed out on it so far? Well, there is a third restriction listed on Chase's gift card website: 

This website does not support online sales of Chase Gift Cards to residents of the following states: AR, CT, HI, ME, NH, NJ, RI, VT. We apologize for any inconvenience.

I presume this is because of the abandonment laws in these days, which require merchants to turn unused gift card balances over to the state. Abandoned gift card balances are a big source of profit for banks and gift card companies, and they might not think it's worth offering the cards if they can't keep abandoned balances.

Now, this isn't an insurmountable problem: I could change my billing address to a state where shipments are allowed, then have the cards mailed back to me in New England. But at that point, there are more moving parts than I'm comfortable with, especially since it's not clear how much longer this opportunity will be available.

No, buying miles and points still (usually) doesn't make sense

On Sunday I described a mistake I made when making an upcoming Marriott reservation: since Marriott allows you to purchase points for 1.25 cents each, if a Marriott redemption makes sense on the merits (I wanted to stay at the airport the night before my departure) then you should buy any points you need. Instead, I transferred super-valuable flexible Chase Ultimate Rewards points from my Sapphire Preferred account, even though those points are worth at least 1.25 cents each when used to purchase paid airline tickets through the Ultimate Rewards portal.

That reminded me of an e-mail I received recently from reader Kimberly in San Diego. She asked:

When I checked in for a united flight from San Diego to Chicago they asked if I want to get double miles (over 1700 extra) for around $60 I think. The ticket was $400. Should I do it?

This is the kind of split-second decision that frequent flyer programs love forcing their customers to make. After all, checking in at the airport you might not have any idea whether this is a once-in-a-lifetime opportunity to stock up on points, or even whether it's a better deal than buying points online at united.com. That's one reason why you should always have a general idea of what a mile or point is worth to you.

Now, some travel hackers take this to extremes and try to establish specific prices they're willing to buy points at and specific values they're willing to redeem points at. Those travel hackers also accumulate vast quantities of miles and points because they're always waiting for the perfect redemption. 

My approach is slightly different, and it works better for my lifestyle: I'm always eager to redeem my miles and points instead of spending cash, but I also only acquire them at the lowest cost possible: that's why I have a single-minded focus on my cost per point. For example, when the no-fee Hilton American Express card gave 6 Hilton HHonors points per dollar spent at drug stores, it was possible to earn HHonors points at a cost of 0.13 cents each. For me, that makes it academic whether I'm redeeming my HHonors points for 0.55 cents each or 0.8 cents each: either way I'm beating the house every time.

That brings me back to Kimberly's question: should she buy 1,700 United MileagePlus miles for $60 when she checks into her Chicago flight? For me there are three numbers that make this decision easy:

• 25,000: the number of MileagePlus miles required for a domestic round-trip award ticket;
• 60,000: the number required for an economy transatlantic award ticket;
• 100,000: the number required for a business class transatlantic award ticket. 

Those are the three awards I redeem my MileagePlus miles for most frequently. And purchasing United miles for 3.5 cents each would value those tickets at $875, $2,100, and $3,500, respectively.  Since I know I would never spend that much money on one of these tickets, I know that I should pass on the offer to buy miles.

Should you care about the 30,000 Starpoint signup bonus?

 It's no surprise that the travel-hacking blogosphere has lit up this week with links to the Starwood American Express personal and business cards, which through September 3, 2013 offer 10,000 Starpoints after first purchase and 20,000 additional Starpoints after spending $5,000 within 6 months. The card usually has a signup bonus of 25,000 Starpoints, so this is a 20% increase over the standard signup bonus.

I've never had a Starwood American Express, so I'm eligible for both signup bonuses, but I'll probably take a pass this year (the increased signup bonus is typically offered once a year). Since this promotion is getting so much play on other blogs, this is a good time to breakdown who this card might be right for. For more detail on all the information below, check out all the Starwood redemption options I explain here.

Hotel Stays

There's no question that Starwood, along with Hyatt and Club Carlson, has devalued their award chart least among the major chains, although the changes to Cash & Points rates did not win them any new fans.

Category 4 properties can cost many hundreds of dollars per night, but cost just 10,000 Starpoints, which could make this signup bonus worth well over $1,000 if used solely for Starwood reservations you were going to make anyway.

Elite Status

Indeed, if you regularly book paid stays with your own money at Starwood properties, then this card is a no brainer, because you probably value elite status highly. Starwood is exceptional among major hotel programs for awarding elite stay and night credit for award stays, so with the 35,000 Starpoints you'll have after meeting the minimum spending requirement, you could make 8 one-night reservations at Category 1 or Category 2 hotels. Those 8 stays, plus the 2 elite stay and 5 elite night credits you are credited with just for having the card, would already get you to Gold elite status (10 stays or 25 nights).

If you direct a majority of your paid stays towards Starwood properties, then elite status could make these cards worth carrying, thanks to the 50% earning bonus elites earn: 3 Starpoints per dollar spent on paid stays, instead of 2 Starpoints per dollar. Plus you'll earn 2 Starpoints per dollar spent on the card at Starwood properties, bringing your haul to around 5 Starpoints per dollar (slightly less, since you won't earn base Starpoints on taxes charged by the hotel), plus any promotions.

Airline Transfers

Like flexible Chase Ultimate Rewards and American Express Membership Rewards points, Starpoints can be transferred to many airlines at a 1 : 1 ratio, with a 5,000 Starpoint bonus at the 20,000, 40,000, and 60,000 Starpoint levels. This naturally creates the temptation to use this card to manufacture spend in order to secure award tickets. Even better, the Starwood American Express has an annual fee of just $65, compared to the $95 annual fee of Chase's flexible Ultimate Rewards cards, or $175 annual fee of the flexible American Express Membership Rewards cards.

You can find Starwood's airline transfer partners here.  The most important programs to note are Alaska MileagePlan, American AAdvantage, Delta Skymiles, and US Airways Dividend Miles. That gives you coverage in all four major alliances and partnerships, at least until US Airways leaves the Star Alliance for oneworld.

Flight Redemptions

Many Starwood loyalists prefer to transfer their Starpoints to frequent flyer programs to redeem for premium cabin tickets. However, Starpoints do have value beyond Starwood stays and airline transfers, so I always try to mention Starwood Flight Redemptions awards, which allow you to redeem Starpoints for paid airline tickets. 35,000 Starpoints can translate into one paid ticket costing up to $215 (15,000 Starpoints) and another ticket up to $280 (20,000 Starpoints), making this signup bonus worth up to $495 in paid tickets, plus the value of the frequent flyer miles you'll earn for those flights.

That's why even if you don't ever intend to stay at a Starwood hotel or book a premium international flight using frequent flyer miles, you may still want to consider this card since the points are between $315 and $495 in paid airfare. 

Drawbacks and Alternatives

Unfortunately, there's a drawback to this card: the Starwood American Express doesn't have any category bonuses except Starwood hotels, which would also be bonused by the Chase Sapphire Preferred (travel bonus) and Chase Ink (hotel bonus) cards. That makes it difficult to justify abandoning a flexible Chase card in favor of a Starwood American Express purely for the sake of manufacturing spend, since the bonus categories of those Chase cards (especially when combined with a Chase Freedom) can be so much more lucrative.

For example, if you have access to PayPal Cash or Vanilla Reload Network cards at a 7-11 that is coded as a "gas station," a Chase Ink card would allow you to purchase Ultimate Rewards points at a cost of 0.39 cents each, compared to 0.78 cents each with the Starwood American Express. That difference means you can pay for the $30 difference in annual fees after just $3,000 in manufactured gas station spending annually.

I consider Alaska MileagePlan miles to be wildly lucrative, since they can be used for Delta or American award tickets (among many other partners). But if you're interested primarily in earning Alaska miles, you can do so with the Bank of America Alaska Airlines Visa Signature credit card (with its annual companion ticket) or with a Bank of America debit card which gives you virtually unlimited free miles earning potential.

Conclusion

Of the three flexible awards currencies, Starpoints are probably the most valuable – each – because of the redemption options outlined above. However, that doesn't mean that the Starwood American Express is the most valuable credit credit to manufacture spend on: depending on your spend pattern, that distinction probably belongs to the Chase Sapphire Preferred or Ink Bold/Plus. Still, "second most valuable" is a strong endorsement, and this is the right card for a lot of people, especially with the current, higher signup bonus.

Right now I'm happily manufacturing spend at 5% cash back with the now-expired Citi ThankYou Preferred offer; 2.22% cash back with the Barclaycard Arrival World MasterCard, during my first, fee-free year; up to 4% cash back with my US Bank Flexperks Travel card; and 1.4 Skymiles and 0.4 Medallion Qualification Miles per dollar with the Delta Platinum Business American Express card. And frankly, that's about all I can fit into my current schedule. In January and April, respectively, I'll lose the first two opportunities and move that manufactured spending onto other cards. At that point I'll definitely consider making the Starwood American Express one of my workhorse cards for manufactured spend.

Buying points: when it makes sense

My regular readers know I have a pretty straightforward approach to miles and points valuation: the least valuable point is the one you don't use. That's why even though I earn hundreds of thousands of points through credit card signup bonuses and manufactured spending, my points balances are often embarrassingly small. 

A good example of this is my Delta Skymiles account, where I noticed today that I only have about 36,000 Skymiles, not even enough for a coach ticket to Europe! And that's despite the fact that I do about 90% of my paid domestic flying on Delta. How did I end up so Skymiles-broke? Because I aggressively look for opportunities to redeem my Skymiles. In addition to my current 100,000 Skymile business class trip to Prague, in the last few months I've booked a 25,000 Skymile domestic award for Labor Day weekend and a 32,500 Skymile domestic award (outbound low-level leg, inbound medium-level leg). All those tickets offered 1.8+ cents per Skymile, so I didn't think twice about redeeming my Skymiles instead of spending cash.

However, sometimes this puts me in a tough position when a situation comes up where I need more miles or points than I have banked in one program.  For example, on my way back from Prague to the States I planned to stay at the Courtyard Marriott Prague Airport, which is about a 3 minute walk from check-in at Ruzyně (now Václav Havel International Airport), and would let me sleep in the day of my departure. This property is one of the great values in the Marriott system: a Category 2 property, costing just 10,000 Marriott Rewards points per night, that can have a nightly rate of over $150 (although rates are much lower on weekend nights).

Unfortunately, even though in April I received the Chase Marriott Rewards Premier card, I had already used the free night and bonus points at the Courtyard Portland City Center back in July for my brother's wedding. My remaining balance: 6,500 Marriott Rewards points.

Figuring I was getting slightly more than 1.5 cents per point, I transferred 4,000 Ultimate Rewards points from the flexible Ultimate Rewards account I have through my Chase Sapphire Preferred card. And then when I went to book my room, I realized my mistake: Marriott Rewards allows you to buy points at 1.25 cents each: I could have purchased the same 4,000 Marriott Rewards points for just $50, and kept my 4,000 flexible Ultimate Rewards points.

Why was this a mistake? Because flexible Ultimate Rewards points are worth a minimum of 1.25 cents each when used to book paid travel.  When transferred to a program like Amtrak Guest Rewards, where the rewards chart is wildly lucrative, they can be worth from 5 to 6 cents each, and with United or Hyatt they'll usually be worth around 2 cents each.

Instead, I could have paid $50 for 4,000 Marriott Rewards points and emptied my Marriott Rewards account without touching my Ultimate Rewards account. Given the potential value of those Ultimate Rewards points, that was the correct move.

10% discount on American Airlines

I've mentioned occasionally that I haven't flown American Airlines in well over a decade: they've always been more expensive and less convenient than Delta or United. But I don't judge (except United), so if you're an American Airlines flyer, be sure to use a 10% off promo code for your next flight. Just play their game, enter your e-mail address, and they'll send you a code. It looks like you can request one code per e-mail address.

I just checked to make sure it's still working, and got this code, which any reader is welcome to use:

BRBPT4X488RS

Note that the code is apparently only good for flights operated by American and American Eagle. 

Delta award availability and @DeltaAssist

There's no doubt about it: Delta has a terrible reputation for award availability.

SkyMiles are incredibly easy to accrue, since Gold and Platinum Medallion members earn 100% bonus miles on all paid tickets and Diamond Medallions earn 125% bonus SkyMiles. Meanwhile the American Express Delta Platinum card earns 1.4 SkyMiles per dollar at the $25,000 and $50,000 spend thresholds and the Delta Reserve card earns 1.5 SkyMiles per dollar at the $30,000 and $60,000 thresholds.

Meanwhile on the redemption side, Delta has 3 redemption levels (versus the 2 redemption levels offered by most of the other traditional airlines) and availability at the "low" level is notoriously hard to come by.

Personally, I think the two factors balance each other out fairly evenly: miles are about as much easier to earn as they are harder to redeem. On the other hand, there's no denying the amount of frustration caused by the cost of Delta award tickets. I come from a family of Delta flyers, and trust me, I hear a LOT of complaints about low-level award availability on Delta. My brother called me the other day and asked, "Why does an award trip to Indiana cost 32,500 miles?"

I asked him, "How much is a paid ticket?" It was over $600, which would give him a value of over 1.8 cents per SkyMile! That's not bad, especially since as a Gold Medallion he earns double miles on all his paid flights.

Still, I eventually end up with virtually all of my award tickets booked at the "low" level, and I want to give a quick rundown of the techniques I use to make sure I don't spend more SkyMiles than I have to.

Before you Start

Before you start looking for award tickets, there are two things you should do if at all possible: 

1. Have elite status. Platinum and Diamond Medallions are allowed unlimited, free "Award Redeposit/Reissue" up to 72 hours before an award flight. Importantly, changes are still allowed after you've flown your outbound leg.
2. Have a Delta American Express card. This will give you access to increased economy award availability on domestic routes. If you aggressively manufacture spend, the Platinum and Reserve cards also make it easier to reach a higher Medallion status. Now that the Gold card no longer comes with an annual $99 companion ticket, it's probably only worth signing up for with a monster bonus, like the 70,000 SkyMile offer about 6 months back.

While you're Searching

Since the Delta award calendar function doesn't work, to find low-level availability you'll probably need to search for each leg of your trip separately.

1. Use ITA Matrix to find possible routes, then start plugging dates and legs into the Delta award search engine. I recommend using an "Incognito" or "Private Browsing" window to do this: once the booking engine stops returning any useful results, close the window, open a new one, and continue where you left off.
2. Your total mile cost will be the average of your outbound and inbound legs.
3. The cost of your outbound and inbound legs will be the cost of the most expensive cabin on each leg at the most expensive level on each leg. For example, if your outbound leg is JFK-SLC-LAX, and you have found low-level first class availability for the JFK-SLC flight, but only high-level economy for the SLC-LAX flight, then you'll be charged for first class (most expensive cabin) at the high level (most expensive level).
4. If you're booking an international trip, start by looking for your international flights. Once you've found low-level availability for your international segments, you can start looking for availability for your domestic connections.
5. Use the "Multi-city"  booking function to feed the flights you've found to Delta one-by-one. It helps to take screenshots as you go, or at least write down the exact flights you find.

After you've Booked

If you don't have Platinum or Diamond Medallion status, then congratulations, you're done! If you do have one of those, then you can start looking for better connections and lower-level flights. This is not particularly glamorous, but it's definitely worth it to get the most out of your miles.

Here's an example: for my current award trip, I had my return booked in BusinessElite non-stop from Prague to JFK, and then in economy from JFK to Boston Logan, since that's all I could find at the low level. But every morning as part of my ritual I would log into Delta and spend 35 seconds seeing if any first class availability had opened up at the "low" level. This morning I was pleased to see that it had. As a Platinum Medallion, I could switch from economy to first class on that flight for free (since I had already technically booked a first class ticket: that was the "highest cabin" I had booked on that leg).

If you have a "medium" or "high" level award booked, you can also call in and have the difference in miles refunded if "low" level availability appears.

Schedule Changes

A similar technique applies if you don't have Platinum or Diamond Medallion status: if a significant schedule change happens you can request that your ticket be refunded. However, you only have one chance to do this, so you should wait until low-level availability appears, then request the refund and rebook your low-level ticket.

@DeltaAssist

I've never had a problem simply calling into the Platinum Medallion service line and having my tickets reissued at the "low" level, or in first class – until today, when I was connected to an inexperienced agent who was unable to reissue just my JFK-BOS segment. Instead of following the rule of "hang up; call back," I decided to see if Delta's Twitter customer service team could make the change for me instead. I've used @DeltaAssist for everything from canceling an upgrade request to thanking a particularly helpful phone agent, but I'd never asked them to move me from economy to first class on an award ticket.

It turns out it worked perfectly: I tweeted them my confirmation number and the flight on which first class award availability had opened up, and they were able to reissue my ticket within about 5 minutes. Just another thing I'll be using the Twitter team for from now on! 

Manufacture small amounts of spend with Plink

There have been a couple fun articles recently about the new rebate service Plink, which allows you to earn points worth one cent each towards gift cards (Amazon and Walmart being two of the gift card options). For example, everyone should be doing this, and this is a fun way to get discounts on Sears merchandise.

I want to point out that is it also possible to manufacture spend using Plink and get virtually all your money back (partly in the form of Amazon credit), or turn a small profit. As Frequent Miler describes in this post, first add Kmart to your Plink wallet, since Sears gift cards appear as Kmart purchases on your credit card statement. Then, click through to Sears from the ShopDiscover mall, where you earn 10% cash back on Sears purchases. Then, order a physical gift card for exactly $50. So far, you'll have earned $5 in cash back through Discover, plus 300 Plink points, worth $3 in Amazon credit. Then, go to to a gift card reseller and sell the $50 gift card for $42 (you'll have to mail the card in). For example, here are the current rates offered by a number of gift card merchants for Sears gift cards, according to Gift Card Granny:

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Thus, after buying a $50 gift card, you'll receive back $47 in cash and $3 in Amazon credit.  Of course, you'll have to pay for postage to mail in the gift cards. On the other hand, you can do slightly better than this by clicking through to Cardpool through TopCashBack to earn another $2 in cash back through that site.

Of course, this is a wildly inefficient way to manufacture spend, and there's a lot that can go wrong: Cardpool in particular has a reputation for "losing" gift cards that are mailed in for sale: I myself won't be doing it myself.

Keep in mind that the value of any technique like this depends on the value of each dollar of manufactured spend, and there are cards that would make it somewhat more lucrative: if you ran this hack through the US Bank Cash+ card and had "department stores" selected as one of your 5% cash back categories, you could earn $100 per quarter this way.

Likewise one of the 4th quarter bonus categories for the Chase Freedom card is "select department stores," and it might be worth running $1,500 through this technique for 7,500 Ultimate Rewards points, especially if you can transfer them to a flexible Ultimate Rewards account.

At any rate, I wanted to make readers aware of this opportunity.