Thinking about spending more time cruising, and the kind of boat I'd like to have to do that.

Now that I'm really retired, I'd like to spend a lot more time on or near the water. Explore the coast. Enjoy quiet sports (bicycling, paddling and sailing). I have time, money and good health all at the same time! If not now, when?

Not everyone agrees this is a desirable pastime. Will probably do a lot of it myself, and will not probably be doing it full time. But that still leaves a lot of room for enjoyable diversion. I've got physical stamina to do it (was able to ride a lot), enough sailing experience to keep myself out of trouble, if I have the wisdom to be humble and patient. Get where I'm going, plenty of technical tools to help with that, and I'm good with tools.

I want to own the means of production, not spend all my time chartering boats not suited to me. I want this in a boat:

small enough to mostly single hand.

shallow draft, the east coast is skinny water

limited bluewater: can comfortably go offshore, not stay there for weeks at a time. e.g get to Carribean, island hop in the trades, venture to south america. Maybe stretch to europe. Around the world is right out, would need crew and a different boat.

Comfortable for hopping up and down the coast, overnight offshore, handle bad weather if / when I get caught out. Live aboard for weeks at a time, mostly at anchor, rarely in marina.

Boats I'm looking at:

Cruiser rated, 25-32 ft, not more than 4.5 ft draft. In the water for less than 50K.

Seakindly motion, propane not alcohol stove, good quarterberth, good autopilot and electronics AIS. Radar optional (for now?) Chartplotter. NEMA 2k network and multifunction displays.

Plan to fill it up with LiFeO2 batteries (super deep draw, quick charge) to power all the autopilot I want, microwave on the hook. Not electric power (not yet). Eventual solar recharge, for now 80A alternator.

Plan for composting head, get rid of 2 throughhulls and a bunch of stink.

Challenge: good dinghy. Ideally rigid and rowable, but hard to store on boat of this size. 8 ft FG would be big enough, maybe can have davits (also good place for solar panels), or nesting, or maybe just tip on gunwale and carry on stern. But these weigh > 60 lbs, too much to manhandle, will need hoists or davits. Are there davits that fold flat? Don't want to depend on towing dinghy in bad weather.

Candidates I've considered so far: (Caveat: I haven't seen any of these boats in person, but I've formed some prejudices based on pictures.)

• Island Packet 27, 29, 31. (these are all + 3 ft for bowsprit) 27s don't have propane, 31s are kind of big for singlehanding (I think now.) 29 is ideal compromise but at the edge of the budget. Great reputation for cruising, tics most of the boxes. Rugged construction, no balsa core anywhere. Not easy to back, and no one claims they're good in light air. SE coast, unlike Puget Sound, is not the doldrums, however.
• Nonsuch Ultra 26: These draw 4.5 ft. Ultra, not classic layout seems better and not the 30, which draws 5+. Unstayed mast, cat rig, great for singlehanding. Comfortable interior. Great reputation for build quality despite balsa cored hull (as well as deck). Would be fine for coastal, including overnight offshore. Questionable for longer offshore passages.
• Bristol 29(.9): Older, full keel but a lot like IP.
• Seaward 28 RK: electric keel, not centerboard; shoal draft 3.5 ft, which is definitely enough. The pics I've seen look very plastic.
• Freedom 33: cat ketch, unstayed. single handleable, though maybe kind of big. Draft < 4 ft!

Candidates I've tentatively discarded:

• Westsail 32: very old now, though still going strong. But kind of big.
• Catalina 290, 30: Not clearly discarded. There are a lot of them, lots of people sail them and prices are reasonable. Good reputation for build quality (to a less-than-bulletproof design point). Better performance than IP, but less seakindly motion. Equally good interior. I'd feel limited to coastal cruising. Maybe that's a good thing?
• Performance Cruising 30, 3000, Heavenly Twins: Initial impression, too cheap a build for extended cruising and living on. I don't have enough multihull experience to feel good about handling bad weather and big seas. My one experience with a Lagoon 42 in chop makes me think I'd never get used to the motion. But enough room, and the option for more speed is good.
• Tris: Contour 30, Corsair 27, etc.: Amazingly little living room in these. Portapotti not head (though could fit composting head). Camping stove, not stand-up galley. OB not inboard. Would be fine for me +1, but not a 2nd couple. Hard to manage in ICW, not built to be all-weather boats. In the price range, but...
• I keep looking at Cape Dory, but they seem old and a bit less livable than IP, haven't found one that appeals to me. But they are considered bluewater and capable cruisers.