I will work longer and get a better/newer boat so I can just fix things as they come up and not all at once.
Strangely, that was part of the logic of our getting a 90% finished custom boat (which never do get to the 100% mark, but that's another story). The boat had a 2005 upgrade of top-end refrigeration, redone interior, A/C-heat pump, minty fresh circuit installations, and various other nice touches. What it didn't have is any kind of a shower facility, no autopilot, no outside throttle shifter, no windlass (plenty of ground tackle, though), and some roughed in outlets.
The electronics are minimal: a 1989 video depthsounder that can be chucked, and a Raymarine 420 plotter from '99 that's maybe good to keep as a helm backup.
What this means is that I have a free hand to install what I want where I want without ripping out old stuff. There is no old stuff, because the previous customizers never put it in.
This is a positive. Sometimes you encounter the "museum piece" boat that ISN'T horrible, because the owners, while keeping the original stuff in good working order, never "modernized" because a two-burner alcohol stove, a 10-channel VHF, an icebox and three 12 VDC incadescents did the trick in 1975 and still do. Nothing may be dangerous (I've seen such boats brought up to code, but not "improved"), but it's easy enough to complicate a boat with gear.
Ever see a wire tail open frame winch for a main halyard? I have on an otherwise quite modernized mid-'70s C&C 35. It's still there because it works and hasn't broken.