I spend a couple weeks each year in Cuba
for work, licensed.
The health insurance
you buy with your visa is inexpensive, and their medical
care is very good.
Cuban people are awesome. Last time I was down there, I was in line at Coppelia with my friend. Coppelia is an ice cream "place", and Cuban institution. They have a place up front for the Yumas and Europeans, where a few scoops cost a few bucks. In the Cuban lines you pay something rediculous like 6 cents a scoop, but you have to have Cuban Pesos, something that tourists don't really have access to but is no that difficult to get from Cubans, or at markets. Anyway, the lines are long at Coppelia, and they have line handlers that seat you in one of several counters in seating areas. This is a dang ice cream complex. We were seated with a couple of guys - you don't just get your own table unless you go to the tourist part, where nobody ever sits together. Cubans will be strangers one minute, and the next, they are like old friends, laughing, telling stories, eating together. These guys bought our ice cream. They remarked that we were eating only two or three scoops, whereas they typically get 5, called "ensalada". These guys had ten scoops each and they were wolfing it down before it melted in the Havana sun.... Long story short, they insisted on buying
our ice cream. They make $20/month.
I'm guessing your friend that visited does not speak any spanish? Not necessary but harder to connect with people if you cant talk to one another. In the hotels they speak english
The place is loaded with Europeans and Canadians and more and more Americans these days with expanded licensed travel. I've carried Euros, CDN, and US Dollars. I have to carry all my cash down there though - no ATM's for US banks........ You do take a hit with the US dollars but honestly I think I'm just going to start taking US regularly now.
Not trying to persuade you by any means, but you should know that besides your green card issue, all the others are really non issues.
Cubans are lovely people. It is very safe down there, as long as you aren't dumb about it and have some street smarts.