Fascinating! It sounds like you want something in place that pushes you to take 1-2 extra trips a year. Maybe you feel like 1-2 vacations a year would be good for your mental health, but you might not take them if you didn't have something pushing you to do it (and not taking the vacations would ultimately be bad for you, all things considered).
Do I understand that right?
Usually I am talking the person through the hidden costs of the "free" vacation: the money spent on hotels, food, alcohol, other entertainment, etc. The extra costs of the vacation often far outstrip the reward of the free flight.
But in your case, you actively want something to push you to take extra vacations... is that right?
PS. The costs of vacations is one case study in the broader issue of the costs of ANY credit card rewards package. The only rewards packages with no counterbalancing costs is where a person has carefully analyzed his spending and he is certain his spending is exactly the same as if he had a debit card. That's hard to be sure of, however. The nature of CC rewards (and credit cards in general) is that they seduce us into spending more money than we would if we had to pull actual paper cash out of our wallet each time (and watch the green stuff go away). The rewards package intensifies the problem: it sets up a subconscious belief that we are making money (3% cashback, man!) by spending it.
PPS. It sounds like you have done some really careful thinking which is great. I will suggest that the correct way to think about these kind of pro-con analyses is not to look solely at the rewards one gets from the card but to compare the same spending with a NAF strategy.
Here's an example. The Amex Blue Cash Preferred gives you 6% back on groceries, 3% on gas, 1% on everything else -- and it comes with a $95 AF. Its NAF sibling is the Blue Cash Everyday which gives you 3% on groceries, 2% on gas and 1% on everything else.
The correct way to evaluate whether the BCP is a better card for Bob than the BCE is not to look at all the rewards and then see if they total to more than $95. That's because he could have also been getting those rewards with NAF cards. Thus, forget the cash he gets for gas and miscellaneous purchases, since there are NAF solutions that give you at least those rewards or better. And with the groceries, he needs to calculate how much he spends there and take 3% of that amount -- which is the additional rewards rate over the BCE. Thus the BCP basically has value if he is certain he'll spend $3200 per year. Even then he might want to raise that higher given that he can get 5% on groceries for half of the year with NAF alternatives (e.g. Discover and Freedom).
Great to see how much thought you have spent on the pros and cons. The important thing is doing vigrorous and methodical thinking.
