I think this is worth looking into, for sussing out his online presence. Where are the best places to play poker online?
I found an interesting
link that has some info on online poker playing in VA. A snippet:
Is It Legal For Virginia Residents To Play Poker Online?
Virginia citizens who want to play poker for real money online at online poker rooms can occasionally find a poker site willing to do business with them, but this site may be operating outside the law. With changes to state and federal laws to make it harder to take part in online poker play in Virginia, changes in other states to regulate and allow online poker seem far off from citizens of Virginia.
I'm thinking he probably played more at a gaming site than a gambling site. Pogo, maybe? Or something similar?