I spent this past weekend in Austin hanging out with a friend who's heavily involved in travel hacking, and he mentioned a few techniques that he had used to manufacture spend, about which he was embarrassed since they seemed unethical to him.
Everyone has different things they’re wiling and unwilling to do, so I don’t blame him for observing different ethical lines than I do. But I also think it’s useful to interrogate why certain activities seem more or less ethical to different people.
Breaking the law is illegal
The clearest cases are when a technique is illegal. With the exception of laws that are themselves unethical, I believe most people, most of the time, in democracies have an duty to obey the law, and in exchange receive the protection of the law.
For example, since structuring transactions to avoid reporting requirements is illegal, and the law against it is basically reasonable, you shouldn’t structure transactions.
Program rules are often written elliptically
Here’s a thought experiment. Delta SkyMiles can be redeemed for passengers besides the account holder. So let’s say your grandfather redeems his SkyMiles for an award ticket for you, then passes away. The ticket is still valid, and I think virtually anyone would have a clear conscience flying on the ticket that had been “purchased” with their living (since deceased) grandfather’s SkyMiles.
But if the account has been closed, I don’t believe it would allow any changes to be made to the award ticket, since Delta’s system treats award changes as first a redeposit of the miles, then a new redemption. Just in case you need to make changes to the ticket, I would find it reasonable to delay notifying Delta that your grandfather had passed. After all, the ticket was purchased prior to your grandfather’s death, so we’ve already established that these are “guilt-free” miles — why shouldn’t you be allowed to use them?
But if you’re willing to keep your grandfather’s account open until your existing reservations have been completed, it’s a short hop to keeping the account open until his existing SkyMiles have all been redeemed for new reservations. If he earned the miles in good faith and gave you access to his SkyMiles account, then what could be unethical about using the miles he accumulated?
Why should you ever notify Delta that your grandfather is no longer with us?
Here's the relevant rule from Delta's online membership guide:
"Under the SkyMiles Mileage Expiration policy, miles do not expire. Delta reserves the right to deactivate or close an account under the following circumstances:
A member is deceased"
In other words, it's up to Delta to cancel your grandfather's SkyMiles account. This is sometimes sloppily referred to as miles "expiring when you do," but that's overstating the case. According to the published rules, miles don't expire. However, Delta reserves the right to deactivate or close dead members' accounts.
The terms and conditions of every credit card I know of states that the purchase of cash equivalents is not eligible rewards-earning activity (although FIA Card Services recently send me a letter telling me I could buy lottery tickets with my Fidelity Investment Rewards American Express). And yet almost all cash equivalent purchases do, in fact, earn rewards. Is earning rewards in that manner unethical?
The key question for me is who carries the responsibility for the enforcement of the agreement. Remember that the credit card contracts you agreed to don’t prohibit the purchase of cash equivalents — they simply say that such purchases won’t earn rewards. Since the credit card companies are the ones running the rewards program, they are also perfectly situated to enforce that clause of the agreement.
In the thought experiment above, Delta can’t be expected to know whether its SkyMiles members are alive or dead. But in the case of the purchase of cash equivalents, the purchase is being run on the credit card’s payment network, being processed by the credit card company, and then being deemed eligible for rewards by the credit card’s rewards program. The customer is making a purchase that is not forbidden by the credit card agreement’s terms.
In other words, if it’s ethical to buy cash equivalents, I don't see how you can have an affirmative duty to notify your credit card company each time they erroneously grant rewards for the purchases.
Conclusion: find the right shade of gray for you
Unfortunately, the vast majority of the techniques we use fall into the vast gray area between the flagrantly illegal and the uncontroversial. If you make a purchase with a credit card, then return the goods for cash, is that ethical or unethical? Does it make a difference if you did so intentionally? How much of a difference? If you return something purchased through a shopping portal and are allowed to keep the points, is that ethical or unethical? If you do so intentionally, on a large scale, after being warned not to, you may end up with date with a US Attorney in Seattle.
Fortunately, man is a morally calculating animal, so the answers to those questions (and more!) are available to anyone willing to think about them.
On the other hand, there’s no guarantee we’ll arrive at the same conclusion!
That’s why the decision of what techniques to use is an essentially personal one. We can try to reason our way through these questions, separately and together, but at the end of the day the only advice that matters is not to do anything that you consider unethical, and try to give everyone else the benefit of the doubt that they’re doing their best to behave ethically as well.