1) Crowdfund $25,000 in mortgage capital.
2) Buy an entire block of properties in downtown Veraderro (15min drive from all the resorts)
3) Scrub off all the black mould (cuz holy shit there's alot of that stuff)
4) AirBnb is available in Cuba now. Rent the property out to snowbirds for $500/month.
5) Hire the family next door to act as the property manager, kitchen staff, and cleaners for $5/week.
6) Buy a bunch of dollar-store wrist-bands so your tenants can sneak into the resorts for the beaches.
That or start a condiment empire. Their food is shit because they don't even have ketchup. Start a website for shipping hamburger helper and powdered gravy to restaurants or communities in bulk.