I went, but it was 10 years ago, so my info is out of date!
We went the same weeks as you and caught the tail end of a hurricane, nothing major, just the outer bands. It was spectacular!
We didn't want a huge resort, so avoided Varedero, and the Cays, and went instead for a resort just outside of Holguin, on the Playa Esmeralda beach. And even then we made sure we were outside the main town there, can't remember its name, as the main town was really touristy as well. We stayed in one of a group of three hotels at the time called the Sol Rio De Mares, there were 3 hotels sat on a cove seperate from the rest of the resort. You could use all the facilities in each hotel, we had a great time.
I would definetely take a couple of days in Havana, we only had one and it was not enough. Santiago de Cuba is worth a visit too.
Eating out was odd, it was mostly state run little restaurants at the time, so we tended to eat in hotels. Food was ok, there was a lottle of rice and beans and fish and goat I think.
The poverty is shocking, and at that time you had to use US dollars to buy stuff it was illegal for a tourist to carry or use the cuban currency. But that's probably changed.
I'm sure someone will be along with more info that's a bit more recent! We loved it and will go back when the kids are older.