JeffKSU:
For casinos I keep logs of the machine/table number(if possible) dealer name, if i can remember, time I played, what game and what casino. Then the amount won/lost for that session.
For sportsbooks I really dont keep the games logged, I record the amount won or lost on that particular day. If I were to be audited, my records, and bank statements would match.
FREEBIE
I am not to worried about the legality issues as of yet. Where does it say it is illegal to bet offshore. Hell, alcohol causes the world more problems than some one placing a few bets.
The IRS is worried about one thing, and one thing only, that is getting their money. You pay them their cut, and they could care less if you got it pushing drugs.
I have more important things to worry about in life if someone is going to storm my apartment to bust me for placing a few wagers, something I enjoy doing.