We have been to Cuba three times now ('01, '08, '09) and fourth trip is now planned for December.
Over the years the country has changed a lot, the friends who have been there more frequently say that it started 4-5 years ago. An educated guess would be their relationship with Venezuela (oil & co) and China. You see trains from Venezuela and the streets are populated with chinese and korean busses and cars. This year we saw our first Porsche and BMW's, Audi's and M-B's were already a daily sight last year. If you take a taxi, it's most likely to be more comfortable than in the US.
Obviously the common man isn't the one sitting in the Audi but back in '01 you had a lot of people offering you their services of various kinds. It was a struggle for surviving. In '08 one could walk pretty freely, even offers for cigars were rare. '09 it was even more so. In '01 the department store in Havanna was tourists, '08 it was locals. So things are getting better overall.
Anyway, my OH dances salsa so we haven't been there on ordinary tourist trips. We have plenty of cuban friends and a few couples with cuban OH's. Usually there has been dance courses with the local masters, a lot of contact with the locals, dance clubs, live performances, trips to the countryside, homeparties, etc. Cubans handle their issues with dance, rhum and cigars -- not a bad idea compared to the guns and suicides of western world. Despite the political issues people are friendly, happy, outgoing and very lovely in general. A kid learning to dance at early age sounds much better than the kid getting fat and playing his Playstation 3.
One thing you'll notice quite quickly that the people are well educated. One thing Cuba has done right is the education.
The old part of Havanna, Havanna Vieja, is such a beaty that you don't find similar in Northern America. A great deal of it has been restaured, there are several nice hotels around and overall it's a very beautiful place to walk around. The rest of Havanna is, well, a latin mess, but if you like to carry a camera you'll see endless photo opportunities. Something is always happening somewhere, the streets are people's living rooms.
I could say that one will see a lot of poverty, lack of health care and whatnot but I rather enjoy the people and place as they are and not how far they are from my home country. There are many countries that will shock you much more.
If one goes there with the attitude of going to a cheap, exploitable communist country -- don't, stay at home. Havanna and Cuba is a great place to visit with the right attitude.
I would highly recommend one visits the country before it gets spoiled. Unfortunately it is a very realistic risk. Not to mention that the immigration to Cuba is much more comfortable than to the US.. ;-)
PS. Our travels have been Havanna-centered so I'm not saying all of the country is in the same position nor that everyone has equally benefit from the aid from China, Venezuela and others. More political people obviously have more issues to deal with.
PPS. Americans are very easy to spot in Cuba so I'd try to avoid being a stereotype.