Confident Captain is exactly where we are looking. We're looking into how much it'll cost for the powerboat courses. We plan on going down south for the winter once we're comfortable doing so. We still need to figure out what we're going to do job wise but
we figure the lifestyle comes first so we'll figure it out.
Our jobs are in New Hampshire but we're willing to find new jobs, and honestly plan on finding new jobs since we don't make a heck of a lot at the moment. Eventually I'd like to get into the boat repair field. I'm naturally mechanically inclined and it'll obviously be a very useful skill.
Unless you have some great independent wealth you haven't disclosed, it seems to me you're getting the cart before the horse here. At the very least work and lifestyle are greatly interwoven. Without adequate sources of income, you don't just take off south to cruise for the winter. You also don't support a cruising and liveaboard lifestyle picking up minimum income jobs along the way. (A few with sailboats do but they don't keep the boats at marinas).
You don't face a what kind of boat or where to keep it decision. You face a "what do you want to do with your life decision." Not to be a killjoy, but you need to look at education and budgeting income and expenses for the lifestyle you want. Now is the time to be establishing the base that will lead to you having the lifestyle you want. However, if you don't establish that base, you'll never quite be able to achieve that lifestyle.
I don't know your current income but you indicate it's not good. Have you sat down and budgeted the cost of a boat, maintaining it, running it, insurance, dock costs, electricity, and commuting between the boat and your jobs?
I like that you're considering lifestyle important, but it takes some planning and preparation to achieve. What about a family? Do you intend to start one? Now more expenses.
I recall a conversation years ago with an employee who was very undependable as family problems and kids were always keeping her out of work. It was a very difficult conversation. I praised her commitment as a mother and told her family should always come first. However, that didn't mean there were no other priorities and work was important to be able to keep the family first. So her job should come behind family, just not so far behind as she'd let it come.
We're living our dream life today, but it was made possible by all we did in our teens, 20's and 30's. We always had lifestyle goals, but we had education and work goals that would allow the lifestyle to be possible.
Now, I do encourage you still to go talk to liveaboards. Just go to marinas that allow and accommodate them. Talk to the marinas, if you see people circulating during the winter just speak to them. If they're on the dock or land they will be fine. Just don't disturb people in the privacy of their boats. I'd also expand my questions to asking about things they'd learned, that had surprised them about living aboard there, and how they got to the point of becoming liveaboards. When did they start thinking of it and what did they do to get there.
You mentioned you'd like to be in the boat repair field. What part of it? What are you doing to get into that field, to make it possible? It could fit well with living aboard, but it requires training and experience. What would your wife like to do and is it achievable at the same time.
The two of you need to sit and do some real planning about your future. Develop questions, decide where to go for answers, develop goals and decide how to achieve them. Find family members or friends whose advice you trust. Best of luck in doing so.
