I would have fought harder / bought my grandfathers tools that the family sold at an estate sale. I am still only an amateur, and at the time I was just beginning to get into it, but they sold the lot of it at an estate sale. He had worked on everything from cars to combines and even worked on trains for 10+ years, and was all about quality. The few tools I have of his are snap-on. I am sure the family got a grand or so for his tools that had cost him 20X that.
I also would have kept a couple of cars that I sold and probably kept a few guns I have traded off in the past.