A Philoshopical Question
Great question! This is the dilemma which faces all cruisers. I will approach this from the "been there, done that" side. I retired at age 49 with strictly inland lake experience. Our first coastal boat was a C&C 40 (aft cockpit) which we sailed for 7 years. We decided to move to a 41'' Irwin CC after meeting numerous cruisers who owned center-cockpits. Like you, we had no interest in racing. We were seeking a different life style, as well as the enjoyment we get from traveling and sailing.
As I see it there are several very general considerations:
a)(You have already answered this one)Do you want a "performance" yacht? You mention that the only consideration in regards to speed is weather? One of the arguments often made on this BB and elsewhere is: faster boats are safer since you can get from A to B faster. BULL!! You might be able to run from some hard blows, but you can''t run from them all. When you do get caught (and you will), this is when your choice of boats will "come home to roost". I have met very few long-term cruisers (more than 2 years) that are on performance/cruisers. In the long run they all opt for well founded, comfortable boats with little if any regard to speed, how well they point or PHRF numbers. This will be your home. You want to be comfortable at anchor as well in rough weather.
b) The type of sailing venue you are talking about will not require a true "blue-water" vessel. Why spend $ on something you may never need. Also, there are alot of tough coastal cruisers that do just fine for extended island hopping.
c)Single-hand sailing & age. If properly set-up, a 42'' cruiser is easy to single hand. Just use your head. Reef early and pay attention to the conditions.
My suggestion is this: Visit some coastal towns and talk face-to-face with a few couples who are out there doing it. Offer to buy them drinks. You can learn a ton this way. It will be the best $300 you ever spent. (remember, I said YOU were buying the drinks) When my wife and I first made the commitment to cruise we met a couple in Morehead City, NC. We took them to dinner and learned more that evening than we had learned in 2 years of reading. Not any secrets, just straight talk about what it is really like. Instead of dreams, we came away with a true "understanding" and feel for the life style. Most cruising couples are very friendly and open to others who are serious about wanting to cruise.
From reading your post, I feel you are on the right track. Good luck!!!