My best too score came when I responded to a CL ad for a Grizzly 4x6. They were asking $120. I showed up and it was an older widow whose husband passed unexpectedly and left a whole basement shop full of tools. When I went down there, I made some expression about how impressive it was and she said "You know what this stuff is?" I said yes. She asked if a 9x20 lathe with tons of tooling was worth around $200 and a delta 14" bandsaw with huge Baldor DC motor was worth $100. I told her that she had a lot of very valuable stuff and told her I would love to come back and help get things sorted, described, and priced. I just thought that if it were my wife, I would want someone to help out. You know the old saying "My greatest fear is that when I die, my wife will sell all my tools for what I told her they cost".
Long story short, I spent several evenings helping out around there, and each time they insisted I take a few boxes of stuff with me. She refused to take my money. She would ask "are you happy with those items?" and I would say "absolutely" and she would say "then we're both happy, and that's all that matters." So when all was said and done, I paid a total of $160 and got my first little metal lathe, a small CNC milling machine, a Kennedy tool box, and tons of hand tools like files, taps, dies, reamers, counterbores, dial indicators, calipers, drills, stock, etc. I got more or less fully equipped for next to nothing because I wanted to help someone out. Turns out I made a couple of really great friends out of it, which is worth more than the tools. Her biggest concern was that the tools get used, and use them I do!