Would it be too hard to turn popular games like CSS, LOL, WOW, Smite into a gambling scene where players put bets into an escrow, then they play out the matches while escrow spectates. Whoever wins gets the others bets and escrow gets a small % fee? I know many would like to gamble by skill and this would be a lot more entertaining than playing BlackJack.
If you can make your site connected to thier server you can totally make it all automatic escrow match but its not possible .
If you want to make a outside Bid you will have to set time for match or be online most of the day .