I get your point about upgrades. In your position I'd upgrade items that make your sailing and living on the boat more comfortable/easier/enjoyable now. It's your home. Anything can happen in a few years and you may decide on a different path altogether. Upgrades won't increase the value of the boat when you decide to sell, but as a buyer, it says to me that you took care of the boat and didn't neglect it. I'd choose that boat over one with absolutely no improvements since it was built.
This is a very good point. I've been scouting out what it would take to recover the existing cushions. The foam is good but the covers are fugly and worn. And also, getting a decent set of vberth cushions. I contacted catalina and they don't do covers anymore. A new set run in the neighborhood of $3K. I did get the name of a woman who does custom cushions. Even comes out to the boat to measure, etc. Will be talking with her later this week. As for other things. You know, important sailing stuff. Have received opinions from four sailors and they all say my standing and running rigging is fine. And yes, if I did trade up, I could probably work on the engine. I used to rebuild old VW bug engines as a past time back in the day. ;-p
Our first solution was to buy a second boat to use as a "guest boat."
This. Actually, I met a couple who advised getting a zodiac or similar for puttering around the estuary. They said they use theirs to go over to Jack London square as well as hitting various yacht club events along the estuary. Another thing I noticed. People use their dinghies, as opposed to footing it on the docks, to visit each other. I've seen situations where a couple will be sitting on the back of their boat, with 3 or 4 dinghies parked around them, visiting, singing, and pretty much having a great time. It's a rather interesting social phenomenon, imo. Anyway, that couple said a dinghy is a must have for short trips to local establishments. I have also toyed with the idea of getting a sailing dinghy. There are a few (RS, open bic, sunfish, that sort of thing
) that look quite tempting.
Single handling a 30ft wouldn't be a problem at all. I'm on a 32ft boat and she's a breeze to manage. Rolling furling helps, as does self tailing winches. Don't worry on that side of the issue. You may fret a bit over things at first but in no time she'll start to feel like something you can pretty easily man handle around.
Yeah, my worry comes more from the fact that I really need to learn how to sail first. At which point, I'll have a better idea of what I might want should I decide to trade up.
The idea of trading up, is of course, all pie in the sky, way future. At this time, my setup is comfy. In fact, I just picked up an ENO hammock for lazy in the sun reading days. :-)