That's a great OP, and I'm at a place in my life where I really needed it to reaffirm my reason to keep all those tools that I've picked up through the years.

What the heck are you gonna to do with all the specialize bike tools?

I have a few that are no longer needed on modern bikes like Campy drop out alignment tools or crank arm pullers. What to do with them?

Can't sell 'em, not worth anything, but too nice to just throw out. Buy more tool boxes is the only answer.

Some touching stories here that we can all relate to because of our (for the most part) common ages.
It was also very important for me to get all of my dad's tools. Lots of them have "Andy" inscribed in them and they are the ones I cherish the most.

I have very few tools that my dad owned. That's because he didn't own many. By age 14 I had more tools than he ever did by a margin. The stuff I do have doesn't seem to hold any sentimental value because my dad never worked with me on bicycles, karts or cars. He didn't care.

My mother studied 'art' at USC and I have s a few of her "tools." Namely some leather working tools and some inking drafting tools which are very high quality. I don't ink, of course, but before CAD I drew all my plans using her tools that held lead. My mother was never an artist but she could arrange flowers like a pro and sew her own nice clothes. Don't know where she found the time.

When my MIL retired, the old woodshed came down to make room for a swimming pool. My FIL approached me to see if I wanted the wooded tool box stored in the shed. It had belonged to my MIL's grandfather who had been a ship's carpenter in the late 1800s.
He didn't have to ask me twice.
Initially, I cleaned up some of the old wooden planes and made display cases for them and presented them to my MIL and her sister. Many of the pieces rest in the tool box which is in my garage. Some of them are in use from time to time. When I get around to it, I will turn new handles for the draw knife which has his name stamped in it (and still had a decent edge on it when I cleaned it up). Many of the tools had his name stamped on them.
I don't know what will happen to the tools when I am gone, but for now, each time I handle them, I feel I am honoring a craftsman who made wooden pumps for the farmers in the village where he settled when he came home from the sea.

Best
Les

My brother and I are in the process of building a new shop for him. Divorce, 'nuff said.
As we worked together on putting up a mezzanine over half the shop, he lamented that 'The Kids' weren't there to help us and boy were they missing out on all the fun we were having. We've reached the age where we work well together. It's his shop so I do things the way he wants them done. Simple.
When we get to a point where the last piece of the puzzle that is the floor, he jams it in as it fits nice and tight. 'That's a Dad fit' he says. Dad always was one to make things fit just so. He's there with us as we use the hammer he always did. We miss our dad, at least I do. He's been gone now for more than half my life. He never got to meet my son or see him play baseball or graduate with honors as an ME. He missed out on all the adventures my brother has taken us both on with his car collection and racing exploits.
I like to think he'd be proud of what we've accomplished. I know he'd love his great granddaughter's to death.
I have an old wood handled screw driver that was his. As a kid, I always would use it since it fit my hand so well. I have a lot of my dad's old tools in my tool box. Every time I use one I know he's with me there, ready to help figure out the problem.
I really don't know what will happen with all my tools. My son has his own set now and a garage to envy too. I don't know if my daughter will be interested in them either. Her two girls are too young yet to get a read on whether or not they'll take to things mechanical.
Ah well. It won't be my problem to deal with anyways, so why worry 'bout it.

I don't remember my dad ever working on much of my projects. He was not a "car guy" and cars were just appliances. His dad never learned to drive. They had cars, but grandma drove them and he was as hopeless as a 8 year old girl when it came to working on a car. Dad was gone TDY for 3 months at a time, and worked long hours when he was around.

My old box of grandpa's tools had some nice planes, draw knives and other woodworking tools that he likely got from his dad. I gave all of those to my brother, as he worked at a mill work for years. He fixed them up and made them look like new.

I do have one weird looking metric wrench that has Ford's logo cast into it. It must have been part of a tool kit that came with some old car. It too just hangs on the wall as a decorative piece.

I will probably inherit most of my Dad's tools in a few years. My brother is a progressive liberal Methodist Pastor, with no knowledge of how to turn a screwdriver, or do anything for himself.

My FIL has a large shop, with many tools, but my MIL will most likely want to sell everything individually for 3/4 of the original purchase price, and get mad when it doesn't sell....I don't expect any hand me downs from her family.