From the Cuba Money Project, an interview with a former USAID official talking about Cuba. The money quote:
These are political programs designed to get information and political stuff into Cuba. There’s no evaluation team going in there to see how they’re working.
We know that the Castro regime has been in power for more than a half century and is as strong as ever, so that gives us a clue about how they're working. Another similar success case? Iran!
Asked if USAID operated similar programs anywhere else in the world, Hyman cited Iran.
For a great visual check out this sample page of a declassified USAID project for Cuba:
The sad thing, of course, is that the hard core group of Florida lawmakers make it impossible even to shed some needed light on these projects, much less shut them down.