I think this is the best thread ever.
My thoughts are keep all your invoices in a file that can be found after you die.
At least the people who get rid of your stuff will know how much you paid for it.
If you have family members, name them in your will for these items. Do not let your system be sold at an estate sale. If you have a complex estate with multiple beneficiaries the stuff may have to get appraised and likely will be sold at an estate sale and certain heirs will be very unhappy. So simply indicate who will get these individual items and it makes it so much easier and then let them figure out what they do with them at their own pleasure.
Keep all your boxes of course. And make sure people know the value of all the boxes you've been keeping otherwise they'll leave them on the curb and have them picked up by recyclers which is tragic because you need the damn boxes.
Make it as easy as possible for people to deal with your stuff after you leave planet Earth.

