Originally Posted by umguy
But here is my question. Was this like selling miles to a friend or was it to a company? I mean if it was to a friend how would they ever know? I redeem things for my friends all the time (not for money), but how would they know the difference?
The more/closer relationship that you have with the "buyer," the less risk you run. "Giving" a ticket to your brother and he "giving" you $500 probably isn't going to be an issue. Selling it to broker would be worrisome. Selling it on eBay would be account suicide.