I have all too much experience with shipping
to Trinidad, if that's an option for you. It's always a hassle, but I've found it to be a consistent hassle. There's inevitably some paperwork or logistical complication, which usually manifests as a time delay, and depending on the value of the shipment some small amount of bakshish (but usually nothing like what import
duty/VAT would be.) Worst-case scenario was an Engel freezer
that Tropical Shipping somehow didn't fill out a value for on the form...took six months to get it. Fortunately, I'm in the middle of a multi-year refit
(Year 6 as of August 08), so I'm usually not in a gotta-have-it-now situation.
The Yacht-in-Transit thing doesn't seem to be a problem in Trini, certainly not subject to daily whim as you describe. Last year I did have to deputize YSATT to meet with C&E to defend the legitimacy of my Yacht-in-Transit status, but I have to admit that from their point of view, a boat being in the country five years and still calling itself "In Transit" probably looked suspicious. They are, however very
particular about the first line of any shipping document including those magic words. If the shipper somehow misses that detail, you're SOL in terms of avoiding paying VAT.
I've heard many anecdotes about St. Maarten being the shipping destination
of choice in the Carib, but I haven't investigated it myself as I'd still have to get it from there to Trinidad.
If I can add a sidebar to this thread, I'd be interested in knowing if anyone has found a cheaper and/or more efficient alternative to Tropical for shipping down to Trini...??