The two of you have an interesting set of decisions to make.
You want to
cruise, with your kids, but don't want to homeschool. (Believe me, I'm sympathetic to your position. Between my wife and I we have 7 university degrees and we wouldn't think of homeschooling. Not that we couldn't handle the academic part, rather it is the social part. There are lots of developmental things that happen with peers that simply can't be replicated in the homeschool situation. Obviously, that is a generalization and isn't true for everyone, but assuming that you have "typical" kids, there's a lot that would be missed.) You want good schools for your kids. Good for you, that is so important and shows that you have a good sense of your responsibilities as parents.
You have a successful business and have done well in accumulating an impressive amount of savings. Good for you, now you want to make sound decisions for keeping it, yet also have some fun. That fun includes sailing and cruising.
As others have pointed out, the problem comes in finding a place where you can have some sailing/cruising without taking the kids out of school, while also keep your business interests going.
Others have mentioned it, now I'm going to strongly suggest it: the
Pacific Northwest, specifically the Seattle/Bainbridge up to Bellingham area. Why?
1. Some truly excellent public schools. The
Seattle district has some outstanding magnet schools for kids with particular interests. Mercer Island (in Lake Washington), Bainbridge Island (in
Puget Sound, across from Seattle), and Bellingham (up by the Canadian border and close to the San Juans) all have excellent schools that consistently rank as the best in the state. Much of the reason for this is the demographics of their districts: relatively well off, high proportion of college graduates, relatively stable (i.e., not transient) adult population. Now, these are certainly not the only ones in the area, but the reason for suggesting them is #2.
2. Close to the water, if not on the water, good sailing infrastructure and cruising. Water is everywhere up here. If you haven't been here, before, then I can best sum it up like this: It is like living in a national park. Natural beauty surrounds us. The San Juans/Gulf Islands and up to Desolation Sound is simply some of the prettiest sailing you will ever see, anywhere. It is very different from tropical sailing, however! Touch bottom around here and it likely won't be sand, but granite. Some serious tides and currents, too, not to mention
fog at times when you go, "where the heck did that come from?" But, all that is part of the charm. The best sailing is not in the summer, however, since the winds tends to be light, but it is the time for the best cruising, since the
weather is also mild and the days are quite long. The downside is the winter, which although not usually snowy in the lowlands, is cool, wet, and short days. You just have to gut it out until Spring, which is spectacular.
3. I don't know about your business stuff. I have some friends who are RE agents and they say times are tough. But, good people seem to always make it through and if you've figured out a way to do in Vegas right now, then you probably wouldn't have too much of a problem.
4. If I were you, I'd consider holding on to your
Catalina and postponing the cat. The
Catalina is a reasonable sized boat and since your kids are going to be ruled by the school calendar (hence, you will be, too) for at least another 12 years, then the longest you can be aboard is for 6 weeks, anyway. Find a marina for the boat, use it on weekends and holidays and keep socking away
money.
Frankly, it sounds like you're having quite a bit of cognitive dissonance (fancy term for when your gut and your
head don't agree). You find the "idea" of cruising quite attractive (and, it is), but many of practical realities give you cause for concern. My
advice is to pay attention to those -- nothing's more important than your kids and their
health and welfare is an investment not just for you, but for all of us. This isn't to say that cruising with kids can't be successful -- it can. But, it does require alterations and lifestyle choices that, at least right now, you either aren't willing or don't feel capable, of making. Look at
Welcome to Yacht Scud and
s/v Ocelot Cruising the World for examples where it has. (By the way, I've met the Scuds -- their kids have turned out wonderfully.)
Most of the other stuff (cooking and maintenance) is simply a matter of committing yourself to
learning it. Even with your financial resources, you don't have enough to hire people to do it for you. Also, even if you did, you will find yourself in an entirely different segment of the
boating world. One that, to my mind, misses out on much of what cruising is all about. Take some
classes -- you might even find yourself enjoying it. There's something very rewarding about taking on a problem and solving it.
Good luck to you. Keep us apprised of your decisions.
ID