As a Canadian, my personal view on Cuba is that Fidel (& now Raul) aren't Evil; they're just misunderstood.
I can understand that the American Government and possibly a fair portion of the American people were rather peeved at Mr. Castro back in October 1962, but gee 51 years is kind of a long time to hold a grudge ...
Anyhow, in these circumstances I would think that going for Canadian citizenship might be the logical solution particularly if the Cuba factor is going to be a long term thing.