Gringo...we lost our next door neighbors and two kids became orphans when Wave Dancer overturned in Hurricane Iris in Belize...I'm sure Gtod had that tragedy in mind.
Nevertheless, the event was a rarity and it appears the insurance companies have excluded Belize etc. from "the box" as you correctly point out. I'm not sure the boat buckeye might buy would even qualify for offshore insurance or whether he could afford it given his cruising budget so it is probably a moot point. We all know there is a LOT of hurricane activity in the Gulf of Mexico but he is probably safer in Belize or Honduras than Sarasota! The real danger is a passage in an unseaworthy boat with a totally inexperienced skipper.
Buckeye, if you get a sturdy vessel with a good engine and settled weather I still think you could do this as a motor/sail.... on the route i suggested but it will not be a cakewalk.
(Gtod...not arguing that your route is not better. For sailors with well found boats it is. I am taking the what is the quickest way to get him across and near land and able to pull in again approach...with a lot of motoring and waiting for weather as needed.)
No longer posting. Reach me by PM!