You are right Dan, this country is very special. I mean really unique. We never do the vacation-like stuff but I wouldnt say we ended up in what you described as the second option... In fact, Airbnb is growing strong in Cuba and I was surprised by the range of choices we had. However, getting anything from food to basic every day life supplies might still be a major struggle. But its really hard to describe Cuba. I think everyone need to see it for themselves to form an opinion on it :)

Thanks for the comment my friend :) Have a good one!