Hey Michael,
If you're only spending $29 and saving $300 I would say it's worth it. I guess my only thing about it is that you said you have to send in documentation and what not to prove you took the trip. That's a hassle. Maybe you are better off with a different card where you don't have to do that. Either way just make sure you come out ahead with your rewards to make the annual fee and the hassle worth it.
Anthony
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