Boat Choices: Double-Check
Buying a boat is a highly personal thing. With experience we each develop opinions about what kind of boat, and what kind of sailing style, best suits our individual tastes. There are no universally correct answers when it comes to buying a boat to go single-handed voyaging, just as there is no universally correct route to cruise, or reason to go cruising, or wife to marry.
Opinions are likely to be extremely diverse on any topic related to distance cruising. (For example, If I were going to do some distance cruising again, Cape Dories would be way at the bottom of my list, being of a totally unsuitable design and build quality for my purposes, I would never own another full length keel again, and I consider cockpit lead halyards and control lines, [especially the vang and reef lines] to be essential to safely when single-handing either onshore or offshore. BUT that does not make Billpjr wrong in what he is saying, because for his style of sailing his advice represents the exact right answer for him. And in fairness, I am sure that Billpjr would never want to go offshore voyaging in a boat like mine either.)
Getting to my point, and with all due respect, looking at your post it would appear that you really do not have sufficient experience to make reasonable decisions on what type of boat and how it should be outfitted so that she would suit your needs, and your list of preferences includes such a wide variety of boats and features that it would appear that you are really taking a total shot in the dark. Your list includes so extremely different boats in terms of sailing ability, seaworthiness, motion comfort, purpose, and build quality that I strongly suggest that you need to slow down and spend more time learning to sail and and learning about boats.
To begin with, I would strongly suggest that you start with something smaller. None of the boats on your list would be suitable to learn to sail if you wish to learn to sail well. It won''t happen or at least it won''t happen very quickly. The general list of boats and your size and displacement goals are at direct odds with your goal to learn how to sail in a comparatively short period of time. You would be far better served sailing on as many different boats as you can and then buying a smaller boat and doing some coastal cruising until you come to develop a set of preferences of your own. Thisis a much faster and direct approach and one that is more likely to prove successfulin the long run.
I also agree with CT''s suggestion that you do a bunch of reading. Marshall is certainly one good source of info but I would also suggest that you read opinions across the board so that you experience the range of choices that are out there, and the arguements behind them.
I know just how strong the pull of the sea can be but sometimes the fastest way there means taking things a step at a time, running the whole race rather than trying to start at the finish line.