Hi Zenpunk and Merry Christmas!
I'm not from Cuba but I have family there and have spent some time there as recently as a couple of years ago.
If you have any specific questions I could answer, feel free to e-mail me at [email protected].
I was never there as a tourist. Even so, I was always welcomed by the soldiers manning immigration. The people there were friendly and helpful. Just be cautious of people who you don't know trying to sell you things or panhandling. They are pretty savvy about tourists.
My experience is that it is better to take US dollars with you. They spend better. However, don't make a fuss if they return your change in Cuban currency. This is the normal practice. My experience is that most people will not try to cheat you. The only place that you need to look out for would be some of the barrios in Havana. But in most places you are perfectly safe to wander about.
You might notice that sometimes if you walk into a restaurant or other establishment they will turn off the tv. This is because they are sensitive about "outsiders" hearing things that are considered to be "in the family". Also, if you trade in small, private businesses you will be able to find what you want. If you go to one of the "state" stores, it will be interesting to walk into a rather large store and see just a few items for sale on the shelves. The clerks are often also rather testy. I have seen a clerk yell at a large group of people who were trying to make purchases and tell them that she would be back when they could behave better. Customer service, for the Cubans, is almost non-existant.
Probably, most of your purchases will be in the shops and lobbys of the hotel(s) you stay at. I think prices will be a little higher but still a bargain.
Please be sensitive about giving away personal items. You don't want to appear to be too, how shall I say it, showy. If you have family or make acquaintances with friends or family of friends, I'm sure that your gifts will be well receive if given discreetly.
I once asked my friends and family how they got along (financially) at times when they had nothing (literally no food, no clothing available) and yet remained so happy? They told me, "No problem, we just get together and share our misery!"
The roads and hiways are fairly good (generally better than in Mexico) AND you can drink the water! Health care is the best in Latin America. Indeed, one of Cuba's main exports is doctors to many other countries. I know firsthand about medical care as I was injured while in Cuba and was taken care of promptly and professionally. I should mention that I suffered a sever cut to my hand. I teased the doctor. I told him, "I swear you were cleaning out the wound with rum and steel brush!" He laughed and denied it. I still think he used rum - heh, heh, heh.
I think you will have a great time. Also worth noting, all of the people with whom I came in contact regard American people very well.
If I think of anything else that might be of use to you, I will post again. But, if you wish to ask me anything, write to me and I will try to answer. I'm not an expert but I do have first hand experience.
Marcos