Gypsiyee wrote: He has money, poker is done purely as a game and sport. If he's profitable and makes money so what? Not like it's a career choice. What would you prefer he do, mow lawns and skirt around the law and risk getting kicked out of the country for evading immigration laws?
While I'm ambivalent in regards to poker, it's fairly easy to get work in most area's of Florida, if he has any marketable skills, which he appears to.
Any sort of temp work is paid by the hour and generally requires no paperwork and is easy to bypass.
If he has cash and doesn't need it, it's all water under the bridge. Most guys shake their head in disgust at the concept of you having water for lunch, while your nonworking, poker playing dude is lazing it up at home. This isn't about you two, but the whole concept which irks most guys, and it'd probably irk you if you were looking at it from an external viewpoint.
Does the guy pay rent/utlities/etc?
Anyways, seems a good work situation for you, Gyp. I'd do it as long as you aren't killing yourself.