I think you can find many places that might work but the specifics about you, your family
, and budget
start to set limits quickly. Good Internet service
needs an urban area or a wired connection. It is perhaps the most limiting part of your requirements because it forces you to places with enough population to have those amenities. It also means as you say you want to start slow so you'll probably require a dock
with utilities available. Home schooling younger children
can work well if you align yourself with one of the home school
organizations. It's not easy to just do this all on your own. Defining how much Internet
access is actually required is a key issue.
That makes you part of nearly all the boats tied to a dock
any place where the climate is desirable year round. I would say there are no clear choices. You are competing against housing costs locally any place you go. I hate to say it but it really is all about the money
. The planning and preparation you make can help stretch the money
farther but taking a car trip this fall would be a good chance to scout out places you can afford vs places you might actually like. That gap is something that is all about you. A trip to FL would do that well. Once you can get more experience, anchoring
out for extended periods can save a lot of money, but you need to get that far first.
I would continue to poke around CF reading up on the many topics. It can help you think about the mass of details it requires to undertake what you want. The logistics of moving a whole family
adds a great deal to the task list. In the balance of all that you can better decide which places might be the best for all of you. It really is less about what other people do/did than it is about how you think about your family and needs. The amount of preparation required to be successful is tremendous. Just wanting to do something is no assurance you can unless you prepare well. It also needs to be a total family process or expectations become disappointments. On a small boat there is not enough room for much disappointment. A one week run with a charter
company could be an eye opening experience and help you make decisions.