I have had a similar experience as well. There were always four tools that stood out as "my grandfather's," although he had a ton. First would be his old Henry Disston saws. We used these building a tool box together back when I was small. The other three were his old Walker Turner drill press, his HUGE vise and his Mall belt sander. I have all of them now but the vise. I should have grabbed it, but I didn't even think about it. He had a stationary belt sander as well, but I always recall him using the hand-held Mall sander, upside-down, in the vise. Seemed perfectly practical. We used the sander and the drill press while working on pinewood derby cars when I was a kid. Later, after I moved in with him, I would use the drill press all the time when I was working on small electronics projects.
When he died, I grabbed all that I could, but I didn't have a lot of room in my new place for the larger items like his table saw (it was small, but still), stand-alone sander, bench grinder on a rolling stand, etc. I also regret not grabbing his old Milwaukee drill (solid steel - or maybe aluminum - but heavy as hell). I grabbed all of the hand tools that I could and most of the hand-held power tools, but I know I missed a lot of stuff. My grandfather was a pack-rat (I inherited that from him as well) and i'm sure there were things stuffed away places that might have been awesome. I should have spent more time digging - and often think about/regret it!
Cool story about the wrench - definitely a quality item with a lot of sentimental value!
-James