It would be also very interesting to know from where you get that figure that more than 50% of the population support the Castros as that data is famously unavailable.
for the record, it's an effed system and economy and a poor country, just not quite as effed as people would like you to believe. people flock to the US from Mexico too, and that's without the wet foot/dry foot policy giving Cubans automatic asylum.
if they do get decent Internet it will be a pretty good tech hub due to the education. Americans might even flock there for a cheap, beautiful and fascinating place to live. Cubans actually have the full US cable/media package via el paquete and eat it up.
while you're at it, read up on the Fanjuls, some of America's greatest recipients of corporate welfare, and why US sugar prices are a multiple of world prices. if you love free markets, best thing we could do for poor countries is not blockade them while subsidizing politically connected moguls. (who profit from boycott and generated the constant anti-Castro drumbeat and policy...until they decided they'd rather do business with Cuba)
http://www.vanityfair.com/news/2001/02/floridas-fanjuls-2001...
https://www.aei.org/publication/protectionist-sugar-policy-c...
If the United States had a wet foot/dry foot policy with the rest of Central America, it would be absolutely flooded with asylum seekers. It's already flooded with illegal aliens risking their lives, paying coyotes to smuggle them across the Mexican border - imagine what would happen if they were automatically legalized.
If you're one of the educated white folks whose family lost a plantation or Havana mansion, I can understand you hate the Castros. It's like getting kicked out of Paris and 60 years later the city is literally crumbling. For a while it was like a civilization trapped in amber but infrastructure has gone over the line into complete decay.
On the plus side is good education, good health care, not a lot of crime, until recently a guarantee of a job that would keep body and soul together.
The Castros still have > 50% popular support, they have managed to maintain control of the country and the armed forces despite all their failures, foreign military adventures, withdrawal of Russian support, constant pressure from the USA.
It's a very mixed bag but not the one-sided disaster we constantly hear about from people who make a cottage industry of selling that story (someone has got the US to spend $500m on broadcasts to Cuba no one can receive, and that's just one example).
Moving to a more liberalized economy and attracting foreign investment without causing social unrest, giving up control will be a challenge, and the fact that all the educated people want to leave will not make it easier.
these were interesting http://fusion.net/story/116226/historic-poll-top-25-findings...
http://ftalphaville.ft.com/2016/03/21/2157021/the-us-and-cub...
http://www.newyorker.com/news/daily-comment/cuba-after-obama...
https://medium.com/@dtemkin/spending-the-last-week-in-cuba-w...