Cuban Pirate/Vikings!
Thinking about it (I tended to think about the NE in the US), I would agree that unless the Cuban people were extremely unhappy with the Castros, while they might lay low in 1997 & 98, by 1999, I have trouble seeing how they could resist tweaking Uncle Sam's beard - kicking the fallen giant.
No need to keep and hold turf (though some central/southern Florida cropland would not have been a bad thing) - raid!
Cuban soldiery raiding, using small flotillas of fishing boats. Land, shoot up any resistance, and make off with food, weapons, finished goods.
Cuba, actually, is well set up for 1997 and a cutting off of Soviet-supplied oil in that they have industrial-sized distilleries and grow sugar cane. No, you cannot fly aircraft using it, but you can power motor boats and vehicles.
It's got possibilities.
"Today, the forces of the People's republic of Cuba brought enlightenment and freedom to the town of Jupiter, Florida, ending a reign of terror by its local police. The grateful townspeople donated 4 tons of canned goods, a ton of recently harvested oranges, and two 20-ft sailing vessels to the free people of Cuba. Viva la Revolucion!"
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