I haven't had time to read the whole thread, so maybe a good solution has presented itself. If not, and coming from one who actually HAS replaced a mast in the
Caribbean, as opposed to just hearing about it, I would say:
1) First, I would check carefully with the insurer. Often there is a residual value, after all depreciation has been taken, and it may well be 20%. That is worth fighting for, so I would get serious about that and really read your policy.
2) There is technical assistance as good as there is in
Florida in a number of islands. Specifically, this would include
Puerto Rico, the
BVI, and St. Maarten, and, maybe the USVI, although they are not that well set up for this. I replaced my mast in the
BVI.
3) I doubt if it will be cheaper in Ft. Lauderdale, although it might be, elsewhere. And, none of the places I mentioned is going to charge an exhorbitant duty. There will be some, in the BVI. The USVI will charge for a mast not built in the US, and they will ask for proof. I have had to pay for Trojan
batteries there, which were made in
Mexico.
4) The big problem is
shipping. Your mast is over 40 feet, so it will be shipped in two
parts and then spliced (quite routine) unless it goes
deck cargo, which might be pretty vulnerable. Check shipping schedules.
5) In the PR, USVI, BVI, St. Maarten area, don't expect to find a pile of used masts. They were almost all used after Irma, so you are probably talking about a new one. I have no idea about the
Bahamas, so can't comment, but don't be surprised if there aren't many. In hurricanes, masts are very vulnerable to damage, and are one of the more costly things to replace, but, as I said, I have no personal knowledge, regarding the Bahamas. As has been said, you might well find one in the US.
6)With regard to heading back to the US, or continuing on East, the worst aspect of going East is not that you will be motoring; you would probably be mostly doing that, anyway. But a lot of a monohull's stability is provided by the inertia of the mast. When dismasted, a
boat is way more rolly, sometimes to the point of abandonment. So, take more than the usual care with
weather, and really avoid periods when the northern swells are big. If you could arrange some sort of jury rig, it might not help you sail, but it could help you steady the boat, maybe quite a bit. The worst bit will be before
Puerto Rico. If you can go around the southern side, everything should be manageable, through the BVI. Crossing from there to St. Maarten will almost certainly be a bitch.
7)To some extent, the same considerations would apply, heading back to Florida, but there is more shelter from everything, and you would be doing more downwind
work than going the other direction. But, be careful timing your crossing of the
Gulf Stream, due to the vulnerability from rolling in beam seas.
8)Be carefully if you
head east and plan to use Ocean World, in the DR, as has been suggested. It is super rolly.
Boats break docklines there!
Hopefully, your kitty has just buried itself somewhere safe, rather than
overboard, and will emerge. Best of luck with that, and with everything else.
Cheers,
Tim