Welcome to the Cruiser forum. I'm sure there is just a whole lot here to keep you reading. Please ask a lot of questions and read the various sections.
I guess my question is if you were going to spend forty to sixty grand on a good used boat what would you buy.
$40K to $60K won't get you a really good used boat with a lot of room to be all that picky. Getting a grip on how much space you really need is maybe the hardest part of your task. The second part is living aboard
and having a real life on shore means you automatically have a lot of extra stuff. Extra stuff is not a good thing!
There is only one absolute rule
as far as picking a boat for your purpose - it has to hold you and all your stuff. After that we can get a little more picky - but not all that much.
I'll assume you may leave a lot back on land in storage
. When you live aboard with all that stuff the ability to take off for a quick sail gets to be more of a problem because - all your stuff.
Make the amount of stuff you need match the ability to keep it and in your price
range you won't be looking at a long list of great boats. You'll be looking at a short list of well used boats that need some work. You'll need to balance the amount of work they need, the cost, the on going expenses and the amount of space you'll have.
After that you'll really want to both take a long hard look look and decide if this boat will win an ugly boat contest. If you get past all that you'll maybe have a boat you can like and will work. I see it as a process you go through and not as a list of maybe good boats. I would start by looking at lots of boats, get over to YachtWorld.com and look at more boats and asking prices. You need to come to an understanding of how far the money
will go and how much creature comforts you really need.
You have a lot of hard choices to make but I'm sure you can find lots of good stuff around the forum to get you thinking and maybe after you get started how to deal with the other problems of just owning a boat you live on.