Ahhh, jojo, I may have a work-around for that issue. Still a little risky, but maybe one I'm okay with. I need to do more homework before I'd attempt it. It's on my list though! Everything I see (except that) looks incredible.
Vi, we've done sort of similar trips routing through Puerto Rico to the VI's. Stay a night in Old San Juan, then catch a puddle jumper the next day to the VI's. Not sure if the logistics would be tougher heading to JA, but I'd think it would be do-able with some leg work. I do think our next JA trip will be to Portland though. We seem to need to keep exploring, and not get so comfy with a single destination the past five or so years. JA is always in the rotation though.