Definitely agree with the 2500 at a time method, or maybe 2900, but not more because apparently there is one type of flag at 3000 and another at 10,000. The one at 10,000 is just a form to the IRS saying the transaction took place. You still keep your money but come tax time you'll have some 'splainin to do on your return. If you can show gambling losses or deposits to cover it then there won't be any tax liability, just a hassle of documenting it all. The IRS is not concerned with the legality or illegality of gambling. They just want their tax revenue. Just because you got a check from an offshore casino doesn't mean you did anything illegal. You could have been offshore yourself when you placed those bets and there's no law against that. To investigate your internet usage is separate investigation and is something the IRS will not do unless there are other reasons to suspect criminal activity.
I'd do 2900 a week and send bank wires to Neteller after each one arrives. Once you have Neteller you won't have to worry about this type of shit anymore. Neteller also does bank wire payouts and there are no reporting requirements for bank wires as far as I know, not even for stuff over 10,000.