This is a great thread and very real set of questions, for which I have the following responses bases on what I have done.
(1) First, I think it is important to factor in the kids and where they are in life. Daughter in graduate school now. Until she settles down, she will not want to schlep my 15 boxes and crates of audio gear around. I just don't think they will fit into her Subaru Outback. But I set the stage for her with a McIntosh RS100.
(2) I wrote into my will what will happen with my audio equipment, music collection and artwork. Specially, no Habitat for Humanity, Goodwill or Craigslist for this stuff.
(3) I discussed it with my audio dealer already - If I'm gone and you are still in business, please work on selling them on consignment. I trust they will do it, since they really like my system too and I purchased it from them.
(4) I'm a widower, so no wife to weigh in on what happens.