Hum, a 22 to 24' keel boat is pretty easy to sail single
hand and not too costly to own. An old Oday or Catalina
22, maybe. Docking
is pretty easy in a small boat. If it were me, I'd buy a boat in that range and maybe hire someone for an hour or two to show you the basic's.
22 foot sailboats are easy and basically day sailors with tiny cabins good for an over night maybe. Though pretty cramped for the older backs. (I'm upper 50's BTW) 24 feet will give a bit more room below but still be easy to sail and not too bad docking either. Both would have small outboards for motoring.
Not wanting to raise the mast
, which ok, is a pain for sure, your looking for one you can keep in a slip and NOT on a trailer.
Sounds like you've crewed on a boat, even if just for a bit. As with anything its getting over the fears and just doing it. Starting out on easy days and working up to more wind
as time and comfort level increases. Being crew on another boat is a good way to learn too.
101 would work, its not too costly at all. Its pretty basic, but gives you some time docking and sailing. Enough so its not too scary docking, etc later on. As with all things it just takes practice
I started on 14' to 16' boats a long time ago and sail a 34 foot boat single
handed nowadays. Its also my home, going on 8 years now too. I've sailed a Tayana 37
a time or two single handed, but that's a bit too much boat for me by myself. I found my 34 foot to be just the right balance for live aboard cruising. But I too started on a 22' boat as my first "big" boat.
Here's a link to an older 22' for not too much money
I would look at pre-1990 boats for a learner boat. That way the odd dock
kiss will not be as painful then for a newer $30k boat. Sail it for a year, sell it for about the same cost, then buy the boat you like. You'll have a better idea by then of what your looking for.