I wouldn't worry about a thing.
As for the legality part, you have nothing to worry about. This shit has been going on for years and no one cares enough to do anything about it.
Besides, how could they enforce this anyway?
You have millions and millions of people wagering every day on all kinds of shit.
You have old lady's addicted to online bingo and all sorts of other shit like that.
Hell, they have this shit advertised all over the damn radio, magazines and even billboards when you are driving on the highway.
Do you think this would be allowed if anyone cared?
You don't see signs saying "hey everyone I deal drugs on 29th street and Smith avenue, come get it while you can."
This doesn't happen because authorities care about this shit. They don't want drug dealers out there.
Offshore has never been a problem and it never will be a problem.
In addition to this, if you ask a lawyer who specializes in this stuff, he will tell you that the legal issue has nothing to do with offshore, but it has to do with the state that you live in.
Yes, this surprised me too, but it is true.
Gambling is governed locally, not overseas.
Some states say that is not illegal to place a bet.
For example, in the state of New York, it is not illegal to place a bet. So technically, here you would be fine.
But, I know that in Florida it is illegal to place a bet, so here it would be technically illegal.
Either way, don't sweat it. Even if you are in a state where it is illegal, no one gives a shit.
As far as the taxes, if you are moving very large amounts of money, I would consult an accountant or lawyer to figure out the best way to do it.
If it is small amounts, I wouldn't even sweat it.
If you do decide to declare, you must have specific records of all wins and losses, and you can only write off your losses against your winnings.
If your losses exceed your winnings, you cannot write that off. You just have to eat it.
Bottom line, no one is watching you, so stop being paranoid. I was once like you, so I did some investigating, and now I realize that it was a waste of time.
I was being paranoid too. No one cares about this shit. Don't sweat it.