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When we moved to the farm in 2001, I bought my Dad's 1969 F-100. Dad bought it from the original owner when it was a year old, and I and my brothers all learned to drive in it. I subsequently taught my boys to drive in it out on the hay field.
After ten years hauling hay in wintertime in Central IL, rust was starting to take over. Other mechanical issues brought me to the point where I made the decision it wouldn't be worth the effort to repair/restore the truck. At that time, it would not have brought much money, even repaired (not true today!). So after 42 years in the family, I sold it to a high school kid who planned to 'fix it up' with his Dad.
I saw the truck in town a few times over the next year or two, then got a call from the kid asking if I wanted to buy it back. He had gotten the mechanical issues sorted, but the rust repairs were beyond what he could handle.
I thought it over for just a moment (and was briefly tempted to say 'yes'), but then remembered why I sold it in the first place - I need to 'shorten my lines' on projects and their related expenses - and told him 'thanks for asking, but no.'
Having retired and now being in my 'grandpa' years, I've come to realize that cars and other 'things' are really only temporary, and relationships with your kids and family far outweigh owning stuff.
I have great memories of the truck and lots of photos, and don't regret "letting it go" at all at this point in my life.
Maybe that will give you something to think about in your own decision…