Thoughts on Liveaboard/Cruiser?
Paul, a couple of add''l thoughts...
1. You''ll find every kind of boat out cruising, and I imagine that''s always been the case. But you need to refine your ''needs'' (different from your many thoughts and desires) further before being able to target specific boat brands/designs. I think that''s the point of Jeff''s comments about a trawler.
2. 6'' 8" is a problem. You''ll either need to settle on picking from a much smaller population of designs and buy (literally) into more boat than you otherwise ''need'' OR you''ll have to accept what many sailors with smaller budgets face: no standing headroom except perhaps in a few select spots.
3. $100K - which budget is that? Is it the ''all we want to spend for a sea-worthy boat'' budget? Or is it the ''base price budget''? For an older, larger boat of Taiwan ancestry, you can easily spend $40-50K to insure its reliability and safety. Things like replacing the rigging (standing & running), power train (new engine = $20K), new tanks, upgrading the main 12V wiring with a modern 12V electrical system - and more - are all possible upgrades to such a boat choice. But again, this is also driven by what you actually hope to be doing with the boat and your own set of priorities.
4. Having an open-ended itinerary ("Caribbean first, then perhaps the Pacific" is often heard) is the most expensive, most daunting of goals, because the bar is set so high in terms of onboard spares, basic systems in top shape, seaworthy functionality in every respect for long periods of time, and much more. E.g. just addressing ''chafe'' with an eye to crossing an ocean can be a huge investment in time and clever details; few folks reaching the Caribbean have even thought about it.
For some basic pointers on boat design characteristics and specific designs capable of offshore work, spend some time at John Neal''s site (www.mahina.com/cruise.html) but keep in mind this is one of those ''bar is set high'' sources since he''s talking about extended ocean voyaging. To get your collective feet on the ground, you both should consider reading Ocean Voyaging by Beth Leonard - again, it''s for serious offshore sailing but its big advantage for you is their step-by-step methodology for looking at what you need. She specifically ''classes'' boats into 3 levels of equipment and size, too - something you need to think about more. And I very much like how she approaches the financing of cruising, conceptually speaking. Lots of good value in that reading. And finally, when sorting thru specific systems needed, use Nigel Calder''s Cruising Handbook...but not so you can fall in love with all the systems he describes, but so you can understand the expense, complexity and effort that a bigger, more systems intensive boat can bring with it. His basic advice on hull design, rigs, etc. is also quite good.
Good luck! Don''t give up on the dream just because some of us are throwing cold water on it - besides, you''ll come to LOVE fresh water at any temp! <g>