I hate having to sell anything. It's never that I 'want' to. I've bought most vehicles, mine and for the family, with plans in mind for when it's first use is up. My older son's '65 Biscayne Wagon in the mid-90s was one. It was an original owner garage kept low-mile 6cyl/3spd basic car. Big, great gas mileage, big and safe, and he could lay out in it at a party instead of driving home. Turns out chicks dug it, too
. My hopes for when he moved on was a 427 COPO Wagon. It was perfect for it, but that's not how it went
When I met my x-wife (sounds funny), who had two kids, I got a '55 210 Wagon. It had a 350/TH350, chrome trim stripped, and painted Root Beer metallic with rallye wheels. It ran along pretty well. Took trips in it, went camping, lots of fun. One thing led to the other and I gave it to my brother.
Now way way back, talking way back, I had myself a '66 VW Bus. I made a camper out of it and gave it a "Baja Bus" treatment (in my mind). It actually was great getting places off road. I traveled cross-country, up and down both coasts, with a few trips in between. I had a Corvair engine to swap in but never happened. My old girlfriend ended up with that one