Sad but true questions for most of us older folkes. My oldest son has a strategy that i should start selling down now, otherwise when I move on he will just bring in a skip and out it all goes. Pretty brutal.
I have multiple hifi systems in different rooms as well as a large Vinyl and CD collection, not to mention Guitars and keyboards. Also a growing valve collection as I tube roll plus acquired spares of my favorite NOS valves for each component.
I am disciplined to maintain accurate records on all my gear, what i payed for them and what i reckon they will sell for, which I occasionally update.
So 2 boys, both in their 30's, oldest has little interest though does like live music, headphones at a quiet level off his phone or computer is all he needs and we have few common music tastes. The youngest luckily has similar music tastes and we regularly do road trips to music festivals. I have donated a system to him, he really wanted my Apogee 8's so I built a system around them, so I assume he will want the pick of the better systems. I don't see an interest in vinyl or CD's, into a full digital world which to be honest i have also embraced over the Covid lock down period. I haven't reached a point (yet?) to give up and sell my vinyl.
Now getting old is no joy, having put both my parents into nursing homes with one still alive, at 93. So I also contemplate which of my systems can be used if and when i reach that stage though hopefully I can be home nursed and keep my main systems. I purposely designed our house (build 8 years ago) to support home nursing, my wife is disabled.
So my strategy is ;1) whilst i still have my marbles at some future point I will have to rationalise the many systems and make a call on CD's and Vinyl
2) I really hope to stay in my house as long as possible so I can maintain a couple of hifi systems
3) my youngest can take what he wants when i am gone and him selling the rest by consignment makes a lot of sense.