I've put maybe 100 miles on it this summer (put around 5k on the SV). I love that it's an old bike, and different from the million other Harleys I see out there, but I always have that doubt in my mind: Will I make it to work? Am I leaking oil (or more than usual)? I enjoy mechanic-ing, but it's disappointing not being able to ride it more often.
I'm thinking I might sell it, save up a bit, and buy a more modern 1200 Sportster - should be faster, more reliable, etc. I'm just afraid I'll end up wishing I hadn't sold the old girl :P
I'd say let it go if it makes you paranoid all the time and you don't want to go through re-building it and sprucing everything up. Sell it in the spring, though.