Welcome reader Casey!
I tried to answer your question in the comments section with no success; even my shortest version wouldn't fit in the box, oops! Thanks for stopping by... I'm glad to read you are not clueless about castro and che; that, per se, leaves a huge room for political debate.
You question is the million dollars quest. I'll try to give you my view: the opinion of a simple girl that was born and raised under castro's communist dictatorship and who has been living in freedom for merely ten years. (If you dig back in some of my posts, you'll be able to get into more details).
First, in my own experience, I have seen that most Americans are uninformed/ill informed (thanks, MSM!)about the embargo being a legal consequence to castro's decision to unlawfully confiscate (and not properly pay for) American property. That's a legal/judicial process by international laws where you have two choices: either pay for those properties (which never is gonna happen with castro) or face the legal consequences (the embargo in this case.)
I'd say almost the entire world, including Cubans inside and outside the island know the embargo is the one-size-fits-all excuse the commies has been using for 51 years to blame their own failures; from a dengue epidemic to the their socialistoid economic disaster.
Many people --and I will give them the benefit of the doubt and say that maybe, well intentioned-- argue that if we remove the excuse, castro will be exposed. Really? Do we really need to expose him more? Because whoever have not seen in the past 51 years the atrocities of castro and his thugs is, well, because they don't want to...
And how that is going to change the life of your regular average Cuban?
See... you'd have to understand that there are two parallel realities in Cuba: the one for communists, government, military and tourists elites, and a whole different hell hole of life for the average Cuban citizen that has no access to hard currency.
The embargo being in place or not WILL not affect the life of those privileged elites at all. They have always lived --and believe me, will continue to live-- like royalty in the land of slaves. Nor will change the life of the poor souls on the darker side of Cuba's society. More money will end up in the commies' pockets. Period.
Nowadays, one also have to keep in mind that the embargo is more cosmetic that anything else. It has been weakened substantially during the past US administrations and there are only two measures in place: Cuban govt has to pay in cash, and Americans are restricted to travel (directly) to the island.
From a Libertarian point of view, I agree that no government should restrict the free movement of its citizens. But also, from real life experience, I can tell you Americans traveling there will not bring substancial change either; unless they have supernatural powers I haven't seen yet ;)
Cuba has been receiving tourists from all over the world (not only Canadians) for years. Sadly, the biggest majority of them are only interested in the PR-ready Cuba, where they can get drunk and have sex with cheap underage young men and woman, then post their videos/pics online and pretend they are bringing democracy to the island, one mojito at a time...that is.
From the American taxpayer's point of view (because that is what I am now, an American that works her back off and pay her fair -an unfair--share of taxes), extending credit to a communist government that has one of the worst credit/payment records in the world, according to recent stats from the Paris Club, I think that is a terrible mistake.
Who can guarantee me that castro's debts are not gonna be paid by my hard-earned money in the next bailouts craze, when the next US administration happily decides to use the Constitution as their deluxe toilet paper?
Errr...thanks, but no thanks.
Will lifting the embargo bring change and democracy to Cuba?
IMHO, I highly doubt so... Cuba's mess can only be solved by Cubans themselves.
Had the US government been really interested in helping, it would have done it years ago, by simply don't betraying Bay of Pigs. That was the moment. If it didn't happen back then, it won't happen now.
But... where is the hope?! Can something be done now?! --you may ask...
Yes, of course. I think in the this moment, the US can make the difference by supporting that incipient dissident and civil movement that has been growing in the island in the past 10 years, with all those independent bloggers, journalists and peaceful dissidents battling inside the monster and needing basic technology to weaken censorship and repression from within.
Even if we have to do it one tweet at a time. That will help to bring down the wall the regimen has built since 1951.
On the other hand, I don't have a very promising diagnosis for the useful idiots on this side of the ocean, drooling over everything castro. They only cure would be to GO THERE and SUCK IT UP 'till they die.
(I bet you my relatives there will trade places with all the Maxine Waters, Barbara Boxers, Sean Penns and et al of this world in a New York minute)