At the very least he owns the Cafe, him and Nikki, visit several times. Also the shifty manager (blanking on his name) and Pepper work.He really doesn't need anything overly profitable (for tax reasons if nothing elose)....just not a huge loss.
It was what...17mill iirc he cashed out with (or was it 27...I can't remember)? There will be tax gains to pay on that....but even with that...he bought his apartment and drives an average but nice new car...he not flash at all and he bought a few investment properties (which if IIRC...some are commercial he gets paid rent on).
Plenty left over....just one million in the S&P will return him 100k a year, less income tax (if he takes it as income and not accumulation). His only bills are utilities etc...so he owns everything he has, he has no debt...a 100k a year income and still has a good 8 million left over.
He really doesn't need to do anything.