I'm fortunate to have an adult son living with my wife and me so I know a lot of what I have in the way of tools will be passed on to him. Yet, his main interest is entertaining the bass on nearby lakes, so much of what I have done in the way of hand plane and other tool restoration is only vaguely understood by him. He does appreciate my recent efforts to convert to a mainly hand tool shop though.
Having said that I have been in the process of simplifying my acquisition of these tools so he won't have to deal with selling off stuff for which he may not appreciate their value. I have recently disposed of several hand planes, chisels and of course my contractor table saw and dust collection unit. I still have a power jointer and thickness planer taking up space in my garage. I'll probably try to move those too.
In my 12 x 14 basement shop still sit a band saw and drill press. I'll keep those. My cluttered small Sjoberg work bench is barely suitable but I've had it for nearly 20 years and I'll stick with it. A midi lathe and its accompanying utility cart also swallow considerable room.
One thing I know is that my son is an orginazation hound so the shop will be in much better shape after I'm gone.