I actually meant something in the 24-27foot range, NOT to live aboard straight away...and only bought AFTER you had done a sailing course or two, preferably starting with dinghies (nothing will teach you the essentialls of sailing more quickly or "in the bone" than a dinghy, what you learn will help you on a 120foot boat if that is what you find yourself on...)
Do the dinghy course, do the small keelboat course and then you will know something about what you want form a boat, what you like and don't like and can go shopping. Think of it as a free try-out before you invest your own cash. There are just way to many variables available that are entirely up to you and your preferences and no one can help you with advice on those, except to say, learn enough to know what you are looking for.
Your not there yet. It does not take long. Less then six months is possible, as long as you are taking the right steps in learning stuff.
Do not try to live aboard straight away, it is like trying to swallow an elephant while living in a phonebox. Do some dy sails, grow into weekend sails (called camping on board), then you grow the skills of how to effeciently stow things and organise stuff to optimise the tiny space...
Once again, you are not there yet.
There are two ways to solve the problem of lack of experience with boats. One is with money...not your kind of money...The kind that has two million dollars and up as the budget outline for boating, and a good deal more in reserve. this lets you get over inexperience of living aboard by just buying a hulking huge boat that you can rattle around in and clutter up without having to learn how to do stuff efficiently.
You get around not knowing how to sail by hiring a skipper and mate, ostensibly to "teach you" how to sail, but really they are just doing deliveries with you as a passanger.
You get over not knowing the right boat to buy for your conditions by simply motoring everywhere if you have bought too heavy a boat for the winds where you sail, or by replacing stuff that breaks because your boat is too light, sailed wrong, and bumps the bottom with its deep keel. $25,000 a repair? So what! get it done by Tuesday!
You could take this approach, if you had the resources, about a thousand other people have....
The only alternative though, is to actually learn your way up. It does not take tens of years...but it does take some time until you even look like you are really doing it, and then it takes the rest of a lifetime (I apprenticed as a blacksmith/cuttler. My boss said "Life is like this, you just get to the point where you actually understand enough to make the steel go where you want it to everytime...and then you either die or get too weak and old to lift the hammer"). The people that make it look easy...they got that way by learning and then honing the skills over years of learning better ways as they go.
That's it...No other options. Buy the 37foot boat too early and you just end up with a cramped and expensive trailer home without a yard...you will be too scared and not anywhere near skilled enought to actually use it safely or confidently. You will just be one of those guys that lives at the dock. Might as well buy a houseboat, there is at least something honest about that. Don't trade your dreams in order to just be one of those guys, it is sad and a little pathetic.
You can do this...but think in three to five year planning arcs. That is a pretty fast curve to go from zero to solo sailing your own big boat. You really can't rush it faster then that without serious misery and disaster being the likely outcome.
I feel I am nagging you on two seperate threads.
Seriously, just for the record, I admire what the goal is and I have a lot of respect for the fact that having butted your head against a problem that is basically 97% your own ignorance of the field you want to get into, you actually want to know how to improve things and a tactical way of getting where you want to be. That is way better then someone that just bets their head is harder then the brick wall and keeps on slamming. Seriously, kudos to you....And that is why I. and many others around here would like to see you succeed by the shortest and least thorny path possible.
Sasha