Some thoughts on single handing:
I'm 67 and single hand most of the time. Some suggest that a smaller boat is easier to single hand than a larger one. Size is certainly one factor, but it's not quite so simple to say a smaller boat is easier. In some respects yes, but not in all.
I used to own a Catalina 30, which I also singlehanded most of the time. I now own an Ericson 26. In some ways the Catalina was at least as easy if not easier to single hand than the Ericson, though neither is especially difficult. The Catalina 30 was a much heavier, beamier, and therefore more stable platform compared to the Ericson. In that respect the Catalina 30 was easier, in that the motion was more sedate and predictable. The Ericson is actually fairly stable for a 26 footer, but it is still a 26 footer at the end of the day, and the motion is noticeably more quick and sharp. This is something I especially notice when dousing the mainsail in rougher conditions. Motoring head to wind under autopilot while dropping the main, the Ericson would flail about, requiring me to use extra care and effort to avoid being flung off the cabin top while I lashed the sail to the boom. Adding a Tides Track, a mainsail "stack pack," and integrated lazy jacks made all the difference. Now, dropping the main on the 26 is no big deal because I can do it so quickly (it drops like a rock) and save all the final securing for later. I consider this to have been one of the best upgrades I did on that boat, and regard it as a big safety improvement, particularly when single handing.
The smaller sails on the Ericson help a bit, but I did not find the Catalina 30's sails too onerous. Had I fitted the Catalina with a Tides Track and a stackpack as I did for the Ericson, this would have made the sail handling truly trivial on that boat. At some point as you increase the size of the boat wrestling with the sails will become more of an issue for a single hander. But you are talking about 30' +/-, and at that size it should not be a major deal.
Docking and mooring the Ericson solo is easier than the Catalina, though I did not typically have much of an issue with the larger Catalina. Sometimes picking up a mooring in a brisk crosswind was more of challenge in the Catalina; the lighter Ericson is easier to muscle around. Once you go up several feet, though, I think it gets more challenging. So, for example, mooring my friends Beneteau 36.7 was not bad with someone on the bow and another at the helm, but I could see where it would be a challenge to do it solo. I'd imagine I could do it myself in totally calm conditions, but with much of a breeze it could get dicey pretty quickly.
Another important consideration is how you have your various control lines rigged, e.g., for your halyards, reefing, and so forth. Though there are plusses and minuses, overall I'd say running your lines aft to the cabin top is better for single handing. I think it's especially important for you to have a good reefing system in place, and one that you can set easily from the confines of the cockpit if possible. Keeping the boat on its feet is particularly critical when you are trying to do everything yourself. Reef early and avoid the drama.
And finally, I'd say the absolute most mission-critical piece of gear for a single hander is an effective autopilot. My Catalina 30 had a Raymarine wheel pilot. It was fine for motoring and mild sailing conditions, but would struggle to hold a good course when the conditions got brisk. Personally, I'm not a fan, but unfortunately there aren't a ton of options out there. (I've heard good things about the CPT but have no experience with them.) The Raymarine was good enough most of the time. My Ericson 26 is tiller steered, which I greatly prefer, and I have a
Pelagic. I originally had a Raymarine tillerpilot on the Ericson, but was glad to get rid of it in favor of the Pelagic, which makes the Raymarine look like a toy in comparison. It will steer the boat in conditions that the Raymarine won't touch. This is so important for when I need to be freed up to attend to something else, such as tucking in a reef or what have you. Essential equipment!
While I also enjoy sailing with friends, I truly relish the freedom that comes from knowing that I can take my boat out whenever I want. I find that solo sailing is a great way to clear out my head and truly relax. In the size range you are talking about, solo sailing is quite doable. Setting up the boat for it is critical but not especially difficult to do. Maybe at first a way to gain confidence would be to go out with crew but just have them on standby as you try to work the boat on your own. But again, once you have the right systems in place I don't think you'll find it intimidating.