FMR: I am quite inclined to disagree, as long as one is smart with his money. I have a friend who's won many many many thousands of dollars in the past two years gambling on online poker sites (and more in sponsorship for championship series in Las Vegas and an upcoming Cuba trip, but that's another story) ... he started out with online gambling and has never let it dip under his original investment. The anonymity is good too, allows for practice without the embarrassment if you're really bad at it