I can't comment except for my own experience. We visit relatives in Cuba occasionally. When we go, we always had to come up with some excuse to bring medical supplies and leave them there. On one occasion, my mom pretended to be crippled for the trip down so that we could justify bringing a wheelchair. Then she just left it. Same thing would apply across the board for anything you could think of. We'd get a doctor's note, bring along medicines 'for ourselves' then leave them with family there.
The situation is pretty bad there. It's almost like the economy doesn't exist. You can be an architect, for example, but there's really no new buildings going up. You get a coupon book every year good for things like a pair of shoes, but no shoes are being made. People rely heavily on goods and money from Miami. Money can at least buy them non-American imported goods. A friend's family even brought a window down with them once somehow.
Anyway, I don't know everything about it, just anecdotally what we've seen when we made our trips down, plus the stories from cousins who have made it over recently.