Yeah moving out might be a good thing. You could land hard leaving the nest but I'll bet you'll bounce just fine.
The advantage of leaving the nest is you will be way out of your comfort zone and that will help with one of the most important skills you'll use.
You "need" very little to get into sailing, not having the option of getting anything but the minimum will teach you that.
I'd also say to start with a larger boat 27' sounds good but not so large it does not have a trailer. A trailer quickly pays for itself as you can store it in different/cheaper locations and move it to places to work on it. You should do everything yourself, or almost everything.
I don't know what your skill level is but I did have one trainee reporting to me that had no hands on skills. I gave him several work orders to build basic skills like drill and tap holes in metals, then record breaking torque of the various size machine screws and bolts up to 1/2". Of course I then spent most of the day going over the details needed for him to actually do that, like "....put back the 1/2" grade 8 bolt and use a grade 3..." which lead to a 3 hour tour of the bolt bins to explain all the differences. You don't think there is much to a bolt bin until you have to explain it to someone.
If you do your own work you will learn all about stripping rusty old bolts and overheating cheap tools. Maybe contact the local trade college and see about attending some of the hand tools classes. They may also call it Labor training or something. Those classes should cover the basics of tools and fasteners. That way when you put the hacksaw blade in backwards you'll know it first stroke and not figure it out after burning through a piece of work.
A pet peeve of mine is the lack of knowledge in the boat repair biz about different threads, in particular pipe threads. Try to get a class that covers pipe related info. Most boats are depending on these threads and connections to stay afloat so it is good to have a basic idea of how a pipe or tapered thread is handled differently than a straight thread.
Now that I think about it that's what I would suggest. Taking classes in college. Not for any particular trade, unless you have an interest, but to get a leg up on those who have learned along the way. They may have years more experience but many have never attended a class so are not doing things properly (ok even those who have attended class are not doing things properly but at least we often know we are not doing them properly).
If you could get into the first year of Carpentry and Automotive, or just some of the classes you will get a great headstart. Call and find out costs and programs. I have sat in on many classes I never paid for so that might be an option. I never got in for free on any practical classes which you would want to do.
Who knows could help out in lots of other things as well.
Have faith that the oceans are going to rise and flood the world, that plague and pestilence brought on by Climate Change is going to punish us for not believing. Please do as they say it is our only hope. :P