As an Argentinian, having lived in Miami for almost 13 years, I've had the opportunity to know literally thousands of both Cubans and Venezuelans, and in both cases they're very peculiar people.
I've had endless arguments with both, because I fail to understand how an entire country can be dominated by a handful of thugs, and people won't move a finger to change that.
That said, I think any help that can be sent to oppressed people is a good thing. Unfortunately, in my experience, most of that help will end up in the hands of the oppressors, and the victims will see very little (if any) of it.
Either way, I think you have to earn your help. Cubans have been basically enslaved for half a century, Venezuelans for about 2 decades, and they basically do nothing to force a change in their situation. I got my hopes up in 2004, when Venezuelans started to show signs of rebellion against Chavez's abuses, and finally nothing happened. That's the big problem with Latin America as a whole: everybody talks, but nobody does anything. That's not a suitable way to solve any problem.
I'll tell you how. Likewise, in the Soviet Union, 250 million people were simply intimidated and brought to a bestial state, creating a system that was more terrible than the Nazi. Tens of millions of citizens were killed by their own state, by the hands of the citizens of this country. People were exterminated because they did not want to live in a totalitarian society, they wanted to live like people, they wanted to dress nicely and eat deliciously ... And someone was killed simply because they had grievances and power in their hands. The level of sadism that the Soviet Union spawned, multiplied by the number of people who tortured and killed their brothers, most likely puts the Soviet Union in the first place in the world for bastards and misanthropy. And the same CheGuevara, Castro and other "revolutionaries" of Latin America are followers of Soviet ideology, taught from the works and real deeds of Soviet murderers and executioners. And the same Cubans were instilled with a couple of basic rules - be glad that you are alive at all, the imperialists are all around, everyone envies you, everyone is even worse, close your mouth and enjoy!
By the way - think about why in all countries with a totalitarian government any information channels from the outside are necessarily prohibited - TV, radio, the Internet has just been added? Because it is impossible to threaten and lie if people find out that this is all a lie! Citizens of such countries should be informationally underdeveloped, and live with only one problem - where to eat? Where can I get some money? And at the level of genetics - to be afraid to think about a change of power ..