We'll be doing ours legally in Cuba. It may be less hassel to do it in Canada beforehand, but I dont want to take away from the whole reason we decided to do it in Cuba. We have all our documents legally translated and notarized. I have copy of the vows, and we'll translate the marriage certificate when its done and confirm that its all legit.
I think it'll be worth it doing it down there. I hope anyways.
People only hear about the bad experiences, not the good. I'm sure lots of people have been married there hassle free. Just have to be careful of what you do that's all.