Something you didn't mention were the Bahamas, if you consider cruising there something with a centerboard might be very useful. Most any boat will fit what you are looking for so I would scan classifieds being open to all makes. I have sailed in fiberglass, aluminum, steel, wood, and even ferrocement boats. They all have their own "charms" and can fit the bill. One thing that I would think about is how you plan on using your boat. Are you one to tie up to a dock frequently or do you prefer to anchor most of the time. Do you sail with a destination and time in mind only getting so many days or weeks to sail? Or do you wander following the winds? A bigger boat is expensive but has much more room naturally, no matter how much space on a boat a way will be found to occupy all of it.
My boat is a little 1971 C&C Corvette, at only 31 feet long and with nice beautiful overhangs she is very limited on interior space. She is suposed to sleep 4 but I find it would be tight on 2 if you were taking an extended cruise and were not close. Although she is a quick boat for her size 5.5 to 6 kts cruising under sail or power, she can hold her own with bigger boats (barely). I am setting her up for cruising and will have most of the gear on board that you would find on a much larger boat. She is a centerboard and I can get her into some much nicer anchorages, running aground becomes less of an issue as all I need to do is raise the board up and turn around (very handy here). Cost has been a consideration, I bought the boat for 3800 but before you go getting all excited I am going thru everything on board. I can haul the boat to do the bottom and it costs half the price of a 40 footer. 5 gallons of diesel can take me 100 miles under motor alone. Dockage much cheaper as well, not to mention that this boat is something you can turn around by hand in a canal very easilly if you want. Everything when dealing with this boat is less expensive than a big boat.
Ive sailed many larger boats and found that they are faster, more comfortable for more people, and have more room for more systems. The heads are more comfortable but how much time do you really spend there? As for storage space, I have found that there is more but it always gets filled up with things that never get used. 50 years ago a big boat was 25-30 feet with a cruiser still being around 30, today people feel the need that a cruiser needs to be 40-50 feet with many being much larger. Whats changed? I know the ocean hasn't if anything the ocean should be getting easier to traverse in smaller boats as we learn more about storms and advanced forecasting.
David, we traded in our 2002 Beneteau 361 this past October on a new Benny 43. The broker is Winters Sailing Center in Riverside, NJ. WE live in Hatfield, PA. It's a great boat and well equipped, which I would highly recommend. We traded up with the idea of living aboard within the next couple of years. She handles rough weather very well. I've had her out single handed on Ches. Bay with 25-30kts winds and 4-5 ft chop. Never an issue with feeling safe. She's fast and makes 7kts under power or sail. Has a seperate shower in the head. Big bed in the aft cabin, great galley etc. I wouldn't hesitate to use her for coastal sailing. Take a peek at her on Winter's Sailing Ctr's website. They have 2 for sale, she's the 2002 named Papillon. www.winterssailing.com