I recently sold my Hunter 340 (fiberglass arch vintage), which I used to sail solo almost as much as with crew. It was very easy to sail, with roller furling headsail (110% only), all lines lead to cockpit, traveler on the arch (can't get hit by the boom unless you work at it), auto helm on the wheel steering, VHF in the cockpit (plus a waterproof handheld in a waterproof bag on my belt, for backup), and even the 22 lb bruce anchor was easy to handle myself with chain and three-strand rode.
Self-tailing winches, though I usually just tailed with one hand while cranking with the other. Diesel inboard. Can't think of what else made it easy. Always wore an auto inflatable PFD when solo, and had the vhf on my belt in it's waterproof bag, and never used the autohelm when out of the cockpit. I didn't want the boat sailing or motoring itself to Canada.
The downside was that the main was very large for the boat size, with the B&R rig (no backstay) and a small head sail. 2+2 battens and a big roach. It was a chore to crank that big main up, especially when I was tired. Lazy jacks helped in taking it down, but they can get in the way when hoisting, so I'd tie them back first. But if I could improve just one thing on that boat, it would have been in-mast main furling. It was an option on that boat, buy mine didn't have it. In fact, the seller sold it primarily because she couldn't manage the main, or so she said.
Just some things to think about. Oh, and I'm in my mid-50's. Got a trailer boat this season so I can try some of the finger lakes and the Erie Canal. Miss the bigger boat already. <sigh>
This was my baby. Full cockpit canvas, too. :neutral:
I don't much care for the 'european' look of it (Roger Long's Endeavour a few posts up is one of the best looking boats ever made, on the other hand), but for sailing solo, it was pretty easy, even in some weather.