The best way to win more games on roulette (or to minimize the risk to lose money on the roulette wheel, if you wish) is to focus on the outside bets. Although these roulette bets do not lead to mind-blowing wins, keeping your bets on the odds/even, red/black, and high/low gives you the highest chances to score a win.

If you want to switch between the "real money" and "play money" modes, then this can easily be done in the lobby of the poker room. Download PokerStars and log in to poker client. In the main lobby, on the upper right corner, you can see tabs "Real Money" and "Play Money".

Real money online poker is legal and available in New Jersey, Pennsylvania, Nevada, Michigan and Delaware. It's also legal in Connecticut and West Virginia, but yet to go live there. The top NJ online casinos and Pennsylvania sites are the leaders in online poker.