Over the winter, I went through many of the heirlooms I've acquired. It took several weeks to pull things out, research them, and catalog them. I documented what they were, who made them, what part of the world they came from, who owned them, and what they might be worth in 2008. I attached or inserted a note to every item with all that info. I also kept copies of the notes & put those in a 3-ring binder.
I've told DS many times over the years that family items are valuable to us in more ways than one, and that we should be honored to have them in our care. He can decide, after I'm gone, whether he will keep these things going in the family (I hope he does) or sell them. If he does sell them, at least he will already have the information/documentation he'd need to ascertain their value.
The most valuable things are locked safely away now. I do like them and use them, but I don't want them sitting out all the time for safety reasons. I have many cupboards full of old things (dishes, etc.) that are sentimental and somewhat valuable, and I can get my hands on those readily to use them. I also use my own china, crystal, etc., and that stuff is kept front & center. So if anyone needs to go through my stuff, they will quickly see....."Oh - that was her stuff....that was her mother's stuff....that was her grandmother's..." etc. etc.
For little sentimental things (programs from events, news clippings, letters, cards, etc.), I use those photo/VCR tape storage boxes, one for each year. I drop things in throughout the year and then at the end of the year, the box is stored away. DS can look through them someday & decide what to keep. I didn't want that stuff all over the place, so it's neatly contained by year. The things in those boxes will give a lot of smiles, laughs, and memories someday. I wish my mother or grandmother had done the same, even with just one box!
As far as my "everyday" things, I fully expect most of it to be given away or tossed after I'm gone. My room full of sewing stuff, I've already told DH to sell some & donate some to my friends in my sewing clubs.
I'm seeing DS take more of an interest in family things lately. He was very inquisitive about the family tree and family history while I was going through the heirlooms. A few of the things I did send to him -- books, art work, papers, trinkets, and little things he can take on at this stage in his life, with many career moves still to come. When he "settles," I will pass more things on.
So I'm not too worried about what will happen after I'm gone. I'm keeping that in mind as I go through the house. I feel as if I've planned as well as I can.....and much better than the generations before me did.