[ayamaguc]

My analogy would be a casino comping a player a hotel suite. Would the fair market value of the room offset any winnings a gambler might have?

Yeah, I don't know how comps work. I might guess that by giving you stuff the casino is assuming that you're losing (at least theoretical dollars over the long run) b/c the games have a house edge. So as long as you keep wagering you're theoretically losing. As long as you're losing the IRS doesn't care. Plus valuing comps could be hard? Don't know.

I do know that the IRS decided a while back that frequent flier miles are tax-free (in a situation where you receive them for business travel that is company paid). It wasn't so much that the IRS didn't want the money for what it saw as non-cash compensation, but that they were impossible to value due to the many and constantly changing variables relating to redemption.

So maybe the answer to your question is to collect all of your rakeback in 'leopard print thongs' as someone posted to me here a long while back.