No. Don’t do it unless you’re goal is to loose money.
Forget about the contract. Do you know Cuban law? When the guy breaks the contract or can’t pay you, what is your recourse?
Paladares and Casas Particulares pay very high taxes and can be shut down by the government for no reason including the fact that the owner is getting money from you.
If you want to give the guy money and eat and stay for free, that’s probably your best case scenario.
As far as an investment, forget about it.
Great idea though but it’s a big loser. Post Castro post Embargo, sure, go for it. Maybe give him money for a long long long long long term investment that MAY pay off if and when the Cuban government actually encourages paladares and casas particulares instead of taxing them out of business.