Don't forget option #3, find some desperate american chick to marry for citizenship.
I'm sure my girlfriend won't mind


Seriously though, thanks for the replies.
Obviously this is really complicated. Will talk to a "professional" about this. Probably best to have an offshore trust in the Caribbean. Work from there, six months a year and spend the rest over in the U.S. if I can get the extended visa work.
Tourist visa is roughly 3 months a year.