Please tell me it is worth it???
My wife are very close to where you are at. We did a trip with ''The Moorings'' down in the BVI and this kind of sealed-the-deal. We have been boat shopping for longer than I can remember. Just got back from a day of workshops on maint. . We have lessons/certification scheduled for 2nd week in June. Sorting through ALL of your stuff you have accumulated over the years is a riot! I saved THIS, for what? Slowly we have whittled down to about half of the stuff.
We do plan to spend light and keeping the ''systems'' simple and reliable. Plumbing, electrical, rigging, that sort of thing. Upgrades are in the plans and we plan to do much of them. The phrase " A bank full of money beats a large boat tied to the dock everytime." sure applies to us. After a year we are going to evaluate our Happiness- if either one of us is truely unhappy we will both move back to land. This will be a written agreement. We also plan to work as we go, this will be harder than we think I''m sure.
When we are tired, worn-out, or just plain unhappy while cruising and want to call it quits, we will sell the boat and use our stash-of-cash(from selling our dream house) and start over doing something else that makes us happy. Nothing is forever. I hope this helps.