Well, excuse the pun, but I'm blown away by the great advice and variety of opinion on here! Thanks to all, I'm learning a ton.
What I'm learning:
The big picture I'm getting is that you can do it on virtually any budget, depending on how crafty, dedicated and willing to rough it you are. I'll be having a big discussion w/ financial advisor today to get a much better picture of what I can expect. I am starting to think about supplemental sources of income. I could see working a seasonal job for 3-4 months a year and that basically paying for the rest of the year, allowing my savings to continue growing. I could also rent instead of selling my house, and that would bring in some money, though exposing me to more risks as well. There may be some freelancing opportunities too.
While I want a larger boat 37-40 and to be comfortable, I probably lean a bit more toward Aaron's lifestyle of doing the work myself and figuring out ways to do things inexpesively (but in a seaman like manner). I bought the 37 foot Islander I had in Hawaii for $15k and sold it for $35k after putting maybe $3k and many hours of my own work into her...so I'm a do it yourself kind of person and definitely look for deals. I've broken even on 4 boats I've had and made money on 3 of the boats I've had - a total of $25k in profits. Hmmm...maybe I'll buy and sell boats!
Based on responses I'm also definitely going to expand my search for the boat, both in types of boats I'll consider and regions to shop. I think now that if I don't find a great deal on a great boat in the PNW that when the time comes I'll get a cheap car and just start driving east, looking at boats along the way. The idea of getting a boat in the great lakes or chesapeak bay is very appealing. And starting from florida would work too.
I'm also rethinking what I'll need to outfit with. I think you guys are right - start with the boat as is, make sure it has a bimini, safety gear and motor in excellent condition, some solar power and just start...I can always add stuff as I go and that's sure to save me money in the long run.
Would still like to hear what costs are involved in mooring to buoys, anchoring and docking in the carribbean? I imagine my favorite part of this will be the mix of finding isolated anchorages and spending time anchored outside of small port towns, taking the dingy in and meeting people/exploring, but not sure if there are costs involved or if that's free? Perhaps it varies.