[Faster]

First question... are there areas where you live (or plan to live) where liveaboards are legally sanctioned? or do you plan to live 'on the hook'? (also problematic in parts of Florida from what I've heard)

With kids 2 and 4 you'll have some time to figure out if the lifestyle suits you all before the schooling issue becomes a major one. Are either of you teachers?

For $200K all in you may have some difficulty finding that big a boat, though if you'll settle for older it will be easier.. but upgrades and fixes can run to unexpected amounts.

 

[Faster]

With 200K as a starting point and awareness of need for 'room' for fixes and upgrades you'll have some options.

Here's a couple of pages of a Yachtworld.com search within reasonable distance of your general area with some rough parameters:

(Sail) Cruiser Boats For Sale

I didn't set a filter for age, so you'll have the gamut, but should give you some ideas of where you stand on the boat front. Keep in mind that if you find a well maintained seasoned cruiser it may well have many of the things you'll think you need to add - though some of that may well need upgrading by now. Don't forget, too, that like cars, buying lightly used avoids the initial depreciation and in the case of boats often leads to a lot more of the 'essential equipment' already having been added more or less for free...