Credit cards I'm eyeing for my first round of applications in years

Longtime readers may know that I don’t chase signup bonuses in the way a lot of travel hackers do. This is not because I have anything against signup bonuses, it’s just not something I’ve found to be a good use of my own time and energy. I vastly prefer occasionally picking up cards that I intend to keep more or less forever, either because of their recurring benefits (companion tickets and free nights certificates, for example) or because I have a plan to work them into my manufactured spend strategy.

The one place where signup bonuses are truly irreplaceable is for large expenses that can be paid for with credit cards, especially in unbonused merchant categories. For example, if you have a $60,000 tuition payment you can make with multiple credit card transactions, then even with the highest-earning 3% cash back credit cards your maximum payout is just $1,800. Using the same bill to trigger multiple signup bonuses can easily earn several times that in value, or even in cash.

I anticipate some very large expenses coming up which can be paid across multiple credit cards, which gave me the impetus I needed to put together a round of applications. I settled on a combination of cards that have been missing from my manufactured spend game and cards with recurring benefits and signup bonuses that I’m confident I’ll be able to redeem quickly.

Here are the cards I’m planning on signing up for, and the order I’ll apply in. I’m well below Chase’s so-called 5/24 policy, so I shouldn’t have trouble being approved for those cards, but to stay on the safe side I’m starting with Chase and then working through banks with less convoluted eligibility rules.

Chase Freedom Flex

I have 3 classic Freedom cards and one Freedom Unlimited, but I’ve never had a Freedom Flex so I should be eligible for this signup bonus of 20,000 Ultimate Rewards points after $500 in spend.

The signup bonus is a sweetener but the real reason I want this card is so I can finally product change my 3 remaining Freedom cards to Freedom Flex cards. This is primarily a credit line management issue: I can already earn 3 Ultimate Rewards points per dollar at drug stores with my Freedom Unlimited, but to stay on Chase’s good side I don’t spend more than my credit limit on that card each month. The Freedom Flex also earns 3 points per dollar at drug stores, so having four of those cards will increase the total amount of drug store earning I’m comfortable doing each month, and give me four cards with Chase’s quarterly rotating bonus categories for a total of $6,000 per quarter in bonused spend when promising categories are available.

Chase Ink Business Preferred

For me this is a pure signup bonus play, and I’ll earn 100,000 Ultimate Rewards points after spending $8,000 on the card.

The card does earn 3 Ultimate Rewards points per dollar spent on “shipping purchases,” “advertising purchases made with social media sites and search engines,” “Internet, cable and phone services,” and “travel” but none of those categories are essential to my earning strategy right now, so unless and until the situation changes in the next year I’ll plan on cancelling the card before my next annual fee hits.

Bank of America Alaska Airlines Business

I’m a huge fan of Alaska Airlines and the Companion Fare that comes with their credit cards, but I’ve never actually held one in my own name before. This card has a 75,000 mile signup bonus after $4,000 in spend, plus a Companion Fare the first year and on anniversaries.

The card does have a potential manufactured spend angle in the gas and shipping categories, where it earns 2 Mileage Plan miles per dollar, but I think I’m unlikely to try to aggressively manufacture Alaska Airlines miles that way in the near term.

American Express Gold

I’ve never had a card in the American Express Membership Rewards ecosystem, so my plan is to use this card as my entry point. The signup bonus is for 90,000 Membership Rewards points after $6,000 in spend, and the card also earns four points per dollar spent on groceries and restaurants.

American Express has taken some action to limit abuse of those bonus categories. Venmo payments stopped triggering restaurant bonus spend some time ago, and gift card purchases at grocery stores have also been targeted. I’m fairly confident I’ll still be able to take advantage of one or both of these bonus categories, but if not I’ll simply transfer the signup bonus out and close the card in a year.

Barclay Wyndham Rewards Earner Business

This is a bit of an outlier for me, in that I don’t remember the last Wyndham property I stayed at and have no immediate plans to stay in another one any time soon. Nonetheless, I’ve allowed myself to be convinced by the chorus of cheers for this card that cheap Wyndham points are an outstanding way to book Vacasa home rentals.

This signup bonus offers 100,000 Wyndham points after $15,000 in spend on the card, and the card earns 8 Wyndham points per dollar on gas station spend.

There are a lot of nuances I’ll need to work my way through in practice, but the basic principle of these Wyndham-Vacasa rentals is that points are worth “up to” 1.85 cents each when redeemed for stays that cost exactly $250 or $500 per Vacasa bedroom. The card thus earns up to 14.8 cents per dollar spent at gas stations, when points are redeemed for their maximum value on Vacasa rentals.

More and more of my annual trips are to see larger groups of friends and family, and we often find that renting big houses and condos is the best way to spend the most quality time together. I’m not certain that Wyndham-Vacasa rentals are going to be the perfect solution to that booking puzzle, but I’m willing to give it a year or two to find out.

Conclusion

Across all five cards, I’ll have a total minimum spending requirement of $33,500, which is right in the ballpark of my upcoming credit card expense. Once triggered, I’ll have what I reckon as a conservative $4,150 in miles and points, or a 12.4% return, in addition to the miles and points earned on the spend itself.

That return is so attractive that it’s understandable why, for some people, signup bonuses and travel hacking are synonymous, and there’s no need to touch other tools. Even though that’s not how I choose to play the game year-round, I still know that a big expense you can pay with credit cards is also a big opportunity.