Having actually been to Cuba, I would argue that it's possible to spend most of one's money to benefit private individuals and not the state, if one is in the know. And yes, it's a politically terrible dictatorship, but it's not as competely repressive as others that I have been to or worked in. People shouldn't forget that international politics are complicated, and the US (and the anti-Castro lobby in Florida) are also partly to blame for the miserable conditions in Cuba as well -- Castro appealed to the US for help in ousting Batista, just as Ho Chi Minh appealed to the US in 1945 to help end French colonialism. Trying to portray situations such as this in strictly black and white terms doesn't produce many helpful answers, and demonizing Cuba and Cubans won't help either. As soon as Fidel and Raul are gone, I predict some rapid change between the relationship of the US and Cuba.
Amazing old bikes and cars, by the way. I thought it'd be great when the embargo falls to try to go buy some old stuff up, but the prices are higher there than what one would find in the US.