True enough. 
Thanks for the answers to my questions, and the other information that you’ve posted!
I don’t think I’d go again for the resort, but I think it might be interesting to go to Havana for a week, and then perhaps tour in the country somewhat. Havana has a lot of museums and other cultural activities, like music, that I would enjoy exploring on a free-range tourist basis.
Just realised that I didn’t mention the coconut drinks.
At the shopping mall in Havana, one of the stands provided rum based coconut drinks. The vendor had a stack of coconuts, used a machete to cut off the top, poured some rum into the coconut milk, added a couple of straws, and bob’s your uncle - rum and fresh coconut milk in its original container!
Can’t speak for Piper, but when I went (2014), the questions that got posed to the locals, were more or less deflected. Most of the time, they wanted to hear about your stories about, your home town, your local baseball team and stuff like that.
Usually they gave a safe answer and would expect you to drop the subject, individual Cubans might or might not give a more frank appraisal.
Declan