People have tried this so many times and it always fails. It's a huge issue for going to/from Puerto Rico, due to 1) weather 2) shitty ground services 3) no land connection. My friend has planes and one of them will be part 135 (charter) compatible, so I've been looking at doing monthly flights with a vet and ~10 animals for 2.5h from South Florida to Puerto Rico (especially for people with animals banned on flights due to size or facial structure, or people who value their pets enough to be less price sensitive generally).

(I fly cats for adoption from PR to ATL, MIA, FLL, TPA sometimes; it's interesting traveling with them in the cabin. Usually they are very young kittens and very quiet the whole time.)