The Cuban government recently announced a new easing of their foreign investment rules and are going to allow a number of higher end properties to be developed. If time is not of the essence, you might consider punting this trip a few years and re-considering the destination following the completion of these new developments.
At the same time, it is important to understand some of Cuba's history with foreign capital. In the late 80s/early 90s, Cuba opened its borders to foreign capital and a number of luxury (a phrase I use loosely in this context) properties were built. After just a few years of operations, the government changed their views on repatriating capital out of Cuba, and basically forced out the foreign owners. While the properties are still open in many cases, they are threadbare and in need of significant capital expenditure. That capital, of course, is not forthcoming.
These recent announcements of liberalization may actually be "different is time," and it seems at least one Canadian firm has bit and said they'll invest.
So, if you would consider my "punt a bit" suggestion, be mindful that I'd only ascribe a 50/50 chance to any of these developments getting off the ground.
The other guidance i'd share is to bring lots of hard currency. While non-US credit cards will work in Cuba, friends of mine who have been there report there are few stores to actually buy anything. Of the few they found, cash (not cards or travelers cheques) was the only feasible way to pay.
You certainly won't find a luxury property in Cuba today - holiday inn quality would be a stretch - but you'll certainly have a memorable experience. Not sure if all will be good, but you'll have a lot of memories.
If I were to go, i'd go the day after the US relaxed it's restrictions on Cuba...simply because you'll see a country of new found unbridled optimism ... And I think you'd still capture today's culture, but with a very positive outlook (unlike what they have today).