knew a guy who lived there for a decade. loved it. you can live in Cuba pretty openly, but you won't have legal status as a national unless you marry somebody.
that basically means you can't own a home or be majority owner of a business and you can only be listed on a joint bank account with an actual national.
so if you meet someone you can trust with everything, you can totally do it. otherwise, you'll be kinda marginal status. but the guy was like that and loved it.
**EDIT: dude was a US citizen, from NY. I spent about 2 weeks down there and there doesn't seem to be much popular or institutional distrust of regular ass Americans. people were all pretty jazzed I was from the states, because most honky visitors are from like Europe or Canada. all the fear and aggression is coming from the US.