My Grandpapa died when I was 5; he was an electrician and worked on all sorts of other stuff. Unfortunately, most of his tools were sold around the time of his death. My wife's grandfather owned a freaking independent garage business, but at the time, I had little interest in tools or working on cars, so I got no useful experience from him, and he passed several years after I met him. I have no idea what happened to his tools, but I expect they were sold or trashed.
Both of those things kill me now that I'm a bit older interested in all those things (just turned 30).
I love the quality of old tools in good restorable shape ... bench grinders, drill presses, lathes, saws, vises... I've also been watching more Woodwright's Shop episodes featuring antique tool goodness than is probably healthy. Just haven't been able to locate and/or afford the old stuff. There's not a very strong secondary market for stuff like that in NE Mississippi. Old tools seem to be mainly junk or over-priced. I am also a soon-to-be father, so tool money isn't exactly pouring forth. That's ok. I'll wait, I'll bide my time, and I'll keep looking.