Please remember that playing for real money is a totally different game than play money. So you really want to start at the lowest levels, as you will have to learn the game. 

If you're interested in getting a free $50 bankroll, so you don't have to risk your own money, you can find it at http://www.easy.win/ However, Pokerstars is unfortunately not among the available sites.

If you have not played for real money before I wouldn't really expect to make a whole lot of money in the first 6 months, but after that time you should get an indication if you're a winning player or not.