The year after wife and I got married (50 years ago this summer), we bought our first home from an elderly couple who were moving to a 'retirement community' in Florida. Fred had an old Delta table saw/jointer in the basement that the furnace repair guy had offered to buy from him. But instead, Fred said that he wanted to give the person who bought the house 'first refusal' on the saw/jointer purely to avoid the problem of getting it out of the basement. That was an offer I couldn't refuse!
So 20 years ago, wife and I decided to move to our 'retirement home'. We looked at condominium apartments, but one of the things I put on the list of 'must haves' was basement space for a darkroom and workshop, but nothing offered that kind of space.. So we ended up building a new house - we 'downsized' in that the newer place has fewer rooms, but that's an illusion because it has more square feet of floor space. When we moved, it took four rather burly guys to get that saw/jointer out of the old house and into the new one. And other tools have come along since then including the lathe.
But now I'm facing the situation so many others are in - a time is inevitably coming when we will no longer be able to stay in this house. Our younger son, who lives at home, has no interest in tools or making stuff, and our older son, who might be interested, is semi-retired and living an alternative life style as a nomad traveling around the world with no fixed address. So that presents the challenge of what will happen to my tools when that time comes.
One of my former work colleagues joked that the smart thing to do is plan the future carefully enough that you died before you move out of your retirement home, so that it becomes someone else's problem to clean the basement.
And making it someone else's problem has its advantages. This winter, wife has been going through stacks of pictures that she acquired when she cleaned out her mom's house twenty years ago, and it's been a really painful experience. She has pictures going back more than 100 years - even a few tintypes! Many of the people in those pictures are unidentifiable - presumably they are relatives, but as my wife has no siblings or other close relatives, there is no one who can help - and actually no one who is even interested. So she moves the pictures from one stack to another. She says that she's sorting them out and deciding which to keep and which to dispose of, but it doesn't seem to me that the size of the piles has changed. She has too much emotional attachment.
If it were someone else's problem, the answer would be to park a rolloff in the driveway and just dump everything.