You do have a lot of questions here but let me see what I can do before leaving for my 8:30 meeting. To begin with I would suggest that you are really asking about three different boats, A boat on which to learn to sail, a boat to learn to singlehand big boats, and a liveaboard. While the second two might be the same boat depending on the comfort level that you can live with I suggest that the first boat- the boat on which to learn to sail should be smaller and more responsive. The sailing schools thse days seemed to locked in on 24 to 26 foot keel boats as an platform to teach adults. Learning to sail is not all that hard but to learn to sail really well takes a boat is responsive so that you cna learn sail trim and boat handling. The fact that you are a pilot helps a lot and you get to define the level of expertise that you want to aspire to. Not every distance sailor really is a good sailor. By that many distance cruisers have a near total ignorance of proper sail trim yet they get to where they are going albeit very slowly and/or with more heel angle and leeway than they might otherwise have. There is no sin in that but if you are concerned in sailing well then you might want to consider learning on a smaller, lighter, more modern design than might be suitable.
I suggest that you start out by renting an apartment and buy a boat to learn on. Call it your primary (or secondary)residence for tax purposes. If it has a head, berths, galley and you spend a minimum number of nights aboard (used to be 10 nights but since I paid my boat off I don''t know if it has changed).You will out grow this boat if you want to live aboard but you will also end up a more competent sailor.
Financing on boats can be pretty reasonable. They actually have a smaller forclosure rate than homes.
32 feet is about as big a boat as a person can single hand easily without special gear and special skills. Ideally you will develop the needed skills on your first boat. But an intermediate step may be required to get to the comfort level where you cna handle a larger liveaboard boat by yourself.
When it comes to liveaboard boats I think that 38 feet is as small as this can be done comfortable if you have to go to work and look like you haven''t slept in your clothes the night before. 38 feet is also as large a boat as I think a new sailor can single hand and even then there will be some scary times.
40 to 42 feet can be single-handed but again it ups the anti- a lot. On the other hand since boats grow in all directions there is a lot more room on a 42 footer than a 40.
Liveaboards with jobs typically live with the boats tied up at a dock. Electrical power gets pluged in and in Florida you might have Air conditioning while you are at the dock (AC under way needs a generator which is complexity that I would never recommend) Water can be hooked up with a hose or you fill the tanks when necessary. Waste goes into a
holding tank which means weekly or more frequent trips to the
pump out.
I will talk about specific boats for each type on my next post later today.
Regards
Jeff