A lot of good info being provided regarding the house etc. Not much being said about your child. I have heard the stories about the well adjusted boat kids but I'm not convinced it's a great idea. You seem to have the attitude that her opinion doesn't count because of her age, she isn't going to stay 3. I wouldn't pretend to have the correct answer for your family but I hope that you think this part through very carefully, you are determining your daughter's future.
I appreciate this reply Paul, and I think I maybe mis-communicated my thoughts on her wants\needs earlier. I think I meant more that if I ask her right now "do you want to live on a boat?" she would say YES, if I asked her if she would like to live on a train she would say YES, if I asked her if she would like to live on the back of a gorilla in the jungle...ok well you get the idea.
I figured we could live for 2 years (assuming poor budgeting and all kinds of worst cases other than boat loss or death) if we cashed out now. At that point we would either know if we want to keep going, and figure out how to do it, or we would return and resume careers and also arrive in time for her to attend proper schooling. Her needs are of course first, which is why I think bringing her, at her current age, around the Caribb or South America may be a great beneficial early life experience, but is also why we don't plan on rounding cape horn or anything really risky with her onboard.
Everyone here has given some awesome advice. I appreciate it all and would respond to them all individually but don't want to post-bomb the thread.
My wife as a nurse can keep up her license while we cruise and can basically just walk into any hospital in Canada and get a job anytime she wants thanks to the medical staff shortages here. So that's no concern, at most she would lose a year or two of pensionable time and seniority.
Myself I am a manager within the provincial government which has all kinds of transferable skills to almost any management position private or government. My specialty is in emergency management and I've worked as a firefighter for my entire adult career in various positions and ranks. I have solid references and would be sorely missed by my field if I were to leave, so I do feel like I would be able to land on my feet upon returning, even if it wasn't at the same base in the same job as I left.
Due to both of our careers the option is simply not there to take a few months off to try it out. We have to either go all in or deal with a couple weeks vacation here and there. My only other option would be to try and ask for a 6 month leave of absence and try to do an Erie Canal\ICW\Caribbean run and back in 6 months but that already sounds pressured to me. I think a year would be minimum.