I swooped a Tropicana girl a couple years ago as well. I'll never forget some of the shit she did to me in bed. Lets just say she had some outstanding flexibility.
It's really nice how safe Cuba is compared to a lot of places. I wandered home fucked up to Old Havana during Carnival at like 4 AM and felt relatively safe despite walking around the "edgier" part of the city. I walk around all the time in Cuba, heck sometimes when I'm going home alone I'll walk home several kilometers at 4 or 5am and I've never been on edge. With that said robbery does happen against tourists but it's usually guys walking around with cameras the size of a golf bag and robbery against other Cubans.
I think one thing that throws a lot of people off about Cuba is they see the wages. They then make the assumption that every girl will be in to them. But they forget that while the majority make really shitty wages. A fair amount have lots of disposable income. They aren't paying mortgages, car loans, student loans etc. There are a sizeable amount of people who have money to blow. So while yes, the typical mediocre chick probably doesn't have many suitors who have good financial resources...the more attractive woman still can easily find a Cuban whom does. This is why you still see guys in there 60s rolling with 20 year olds. The 20 year old they are with is far from the cream of the crop... but as they say the worst 20 year old is better than the best 50 year lookswise.
With that said 2 chicks stand out to me as the best looking girls I've ever seen. One was with a Cuban who was young, wealthy (had an audi in cuba, il assume it), deezed guy.
The other was rolling with a Greek or Italian guy who was a bit overweight, 40s, but suited up and had the best table in the club every time I saw him...(seemed he had some kind of gmanifesto game going on).
I think Cuba is a great destination as long as people go with reasonable expectations. It isn't Thailand or the Phillipines.
There really isn't much if any of an expat community which for long term monolingual speakers may be an issue. Personally I like this as it forces me to interact with Cubans. Plus to be honest most of the expats I've met their, seem to start boozing at 9AM and fall asleep after boozing to 10 or 11PM every day. Not exactly my idea of living but to each their own.
Another issue is the lack of ability to just buy a sim card for your phone. Only Cubans can and they are limited to one per person. This makes it extremely difficult to plan dates. When you get a girls number and you have to call her from a landline to her cell phone she has to pay the call! Guess what, at 35 cents a minute 99% of the time she won't pick up and if she does its cause she mistook it for a relative. You can go to some etecsas and rent a phone line for 3 or so dollars a day. But it requires passport, id + paperwork. Not exactly what most people have in mind when going on vacation.
Accomodations are somewhat overpriced in Havana. I think Julio can attest to that. His friends had a place that was 400 dollars a night. While the place was nice and had a pool, in a 3rd world country it's pretty steep. A reasonable place by north american standards will run you around 35 dollars a night. Kind of silly considering I just rented an apartment for one of my girlfriends to the tune of 25 dollars a MONTH.
The other big issue is registering. In everywhere except Havana and perhaps Santiago (not sure) when you bring a girl back she will have to sign a book which is brought to immigration the next day. Her name is recorded and details of the stay. If shes found a few times she can be arrested for a charge that is similar to prostitution. This makes bringing girls to your place an issue. Thankfully in Havana theres a what the eyes dont see doesn't matter attitude in most apartments/houses.
The cops are serious and will stop you walking with girls in Cuba. I was stopped probably 5-8 times this summer alone. Considering all the girls were within 5 years of my age and I tend to lighter skinned ones this is surprising in itself.
1. Police stopped me in a cab home while I was with a gf of mine. (cab driver was his buddy from school thankfully. what are the odds.)
2. Police stopped me in a cab going home a few nights later with the same girl from above (she was white and about 5'11 could easily pass for Canadian based on dress too.) The taxi driver took care of it as they do in the 3rd world.
3. I was stopped when my current ballerina gf took a piss on the street. They radio'ed the police station with her id. Nothing showed up as she hasn't had experience with foreigners before thankfully. This same girl was taken to the police station overnight because she was walking without her ID at one point (not with me). I'm guessing when they called in the details she gave, it now showed up she'd been with a tourist recently.
4. They stopped me while I walking from 23rd avenue to a buddies place with a gay guy and his best friend (hot chica). I convinced the cops I knew her from her hometown and had brought her to Havana with me. She would've been fucked as she wasn't their on a in transit visa as she had gone quickly to take care of her grandma without getting permission. I later banged the hot chica on my buddies bed bareback while he took her gay friend out to buy more drinks
5. I met a girl at a rooftop pool one day with a buddy. Hotel Deuville. Probably the shittiest pool you can find in Cuba. I invited the girl out that night. I happened to invite her out to a bar that is known for prostitution because the bands performing were top class (Charanga Habanera). I went with my canadian buddy, a cuban friend, my date and her sister. Once we left the place they stopped my date, her sister and my cuban buddy. The 3 of them were brought to the station. The sister and my buddy were let go. My date is now serving time...(I was told she must have had a history. But who knows. I called the next day and was told by a guy that she no longer lives there and only found out a few months later when her sister was raging at my Cuban buddy who was with us that night.)
6. I was having a beer with a hooker whom friend of mine walking back from a store. Lone behold a police car drives right infront of us and stops her. They bugged her for about 30 minutes and then let her go.
I tell you this to point out that there are actually risks for girls in being with foreigners. Heck half the cops basically know who I am by appearance in the main areas cause I'm there so much but they still stop me. All of these incidents were in Havana. This is why many girls won't want to go to public places with you. (atleast the smarter ones) unless you seem like a potential suitor. Unfortunately at times I suspect girls who you seemed to connect with choose to not see you again due to this fear or atleast people in their lives telling them about it and I can't blame them. Getting stopped by police isn't fun anywhere. One thing I will say about police in Cuba is they are very polite and generally helpful.
Another recommendation I have is not to ever fight with a Cuban with fists no matter how bad they deserve it. Its pretty common for people to carry small knifes as protection. I don't know anyone who does that in Canada but there quite a few of my friends do. It's not worth it. Who knows if the guy recently had the love of his life stolen from him by some foreigner and hates us all. It's far better to er on the edge of caution. Trust me when I say you will get scammed in Havana and it will piss you off. You will if you are someone who gets even a remote amount agitated (assuming you realized you were hustled) at some point in a week or 2 stay be angry.
I think most guys would enjoy visiting Cuba but only a select few would find it a place they like for longer term stays. Is it a pussy paradise? no. Are there lots of attractive woman? If you go to the right places, even a blind man will say so.