Depending how much you have (I'm guessing about $2500?), you should stay alive betting maybe $25 a hand. Blackjack's your best bet, maybe throw in some European Blackjack or Match Play 21 (in the downloadable client, but fair warning, although there's nothing that affects the game, in other ways it's buggy as hell) to shake it up. Poker room's not going to count the way this works is there's an account you deposit to, withdraw from, and use directly to play poker and bet sports, and one to play the casino, and I'm pretty sure we're talking about the latter, which can't become the former until he plays through $100k.