Steve,
I know exactly how you are feeling. I had my Jeanneau Tonic 23, Spirit, for 18 years and took an extended cruise for two years where I got to know the boat so well that I didn't feel like I was sailing a boat, but I was part of it and we were working as one entity. After buying our camper and property with a cabin, I realized that it was time to sell her, as our interests had changed.
I was able to sell Spirit at a profit, but when the new owner brought a trailer to the yard to take her home, I couldn't watch her being trailered away, so I left before he did. He called me the next spring and asked if I could drive three hours to the inland lake where she was docked to see if he had rigged her correctly. He hadn't figured out the topping lift and had a bungee(!) doing the topping lift's job. He had bent the extruded aluminum toe rail with a ratchet tie-down and the rigging was festooned with pirate flags and all sorts of nylon twirling things. And this was a boat that had taken me safely far south into the Bahamas. He later sent me photos of Spirit under sail, replete with five (count 'em), five fenders hanging on each side.
On a positive note: selling Spirit allowed us to buy Valkyrie, which I can not imagine ever selling and it is now so easy to launch in minutes allows us to use her much more than we could a small sailboat.
Regards,
Nick
"Valkyrie"