I'd choke on 16 grand, too. That said, at this point in my life, with employment and benefits, it would be harder to get months off. If blessed with retirement when/as I hope someday, should health endure, time availability may skyrocket but income drop way down.
I've got one more 'big' trip on the bucket list, no specific plans, just that I'd like to at some point dive a live-aboard in Indonesia (mainly eyeing Raja Ampat, maybe Komodo, Papua New Guinea appeals but isn't part of Indonesia - though West Papua, which is part of the same big island, is part of Indonesia - if I understand correctly). At times Red Sea trips sound both cheap and good enough that if one has the time, and can stand the long flights, that might be an alternative to Caribbean diving. Trailboss123's land-based Philippines trip sounded good; I don't know what it cost, all expenses included.
Before I left for this trip, my wife and mother-in-law took our 6-year old daughter to Gatlinburg and Pigeon Forge in the Smoky Mountains of Tennessee for 5 days of messing around and enjoying some shows. The kiddo mentioned to my wife it wasn't fair I got to be gone longer than they did.
I doubt I'll ever dive Hawaii, because it'd be too expensive to take wife & kid with me, and running off to Hawaii (sort of a brand name paradise) alone might earn serious stink eye from the kid.
Richard.