I don't envy you your task. I dread the thought of cleaning out my parents house when the time comes. I don't have to worry about earlier generations' possessions though. They didn't have much and what little they did have has been taken care of already.

I've been decluttering, not because I'm a pack rat, I'm not, but because I do have a little bit of extra stuff and I want to have an uncluttered easy to take care of home.
One thing I've done which is effective and to me, rewarding, is that I put stuff out on the front sidewalk on trash day with a sign that says free/gratis. It is always taken within an hour and I like to think the items went to someone who really needed them.
I have been doing this off and on every few weeks because doing it all at once would have been overwhelming, and I am just about at the point where it's all done, the garage is organized, and there are no boxes of stuff.
Good luck with your project, don't get overwhelmed because it sounds like you have a lot to go through, just set aside a few hours at a time.

It's a good feeling when "stuff" is gone. I just lack the ambition to keep going, knowing it's going to take a year to accomplish that goal.

We bought an old house that had a container and shed on it that was filled with what I considered,well, crap. Nothing of any value. We arranged to have a demolition/salvage company and cart it all away for about two grand, when i started posting some of the things on craigslist for free. Everything went! I met interesting people who had unimaginable ideas for how they would use every thing. There is also FreeCycle. I found salvage people happy to haul out anything metal -- including tangled christmas lights and fencing. I was happy to save the money, and even more to keep all of it out of the landfill. Many nice encounters in the meantime...

If you haven't tossed it all yet, and I hope you haven't, the family photos may be of interest to a historical society, the letters as well, especially if there are things relating to war times. And you'd be amazed at how many artists use old photos in their work. I agree about freecycle and the free section on Craigslist. Use them before a landfill.

I know that everyone is well meaning when they bring up craigslist, free cycle, garage sales, etc.

But in my experience, that Responsibility to shepherd items to a new home can be stifling. It is OK to just throw things out and not feel guilty about it. It takes a lot (a whole lot) of mental energy to even go through stuff. To add to the process the added task of sorting and then redistributing items that mean nothing to you is not something that you need to do if you don't want to.

It is OK to do as you wish.

Oh I can relate.

DH had a grandmother and an old maid aunt...guess who got all their stuff. His folks had an apartment in NYC and the old house here. Guess who got all their stuff. Then my Mom had to clean out their old house after Dad passed...50+ years of accumulation and both were pack rats. Guess who got a lot of their stuff. She moved into a condo here and had a house in FL besides. When she passed, guess who got all her stuff from those 2 places. Let alone our own stuff and moving out of the old house and into the new house. Is it any wonder we left the upstairs in the new house just attic space? Any wonder that it looks like a goodwill store?

And the tension one suffers between, this is still good, how can I throw it out...but do I really need 14 wooden spoons? And then you get this weird support for keeping it...like when our can opener busted and we just went to the attic to get another one...and there's still another up there...

And trying to get rid of stuff that was in DH's family triggers this strong reaction in him, like a hoarder, that I'm not tossing a dishtowel, but a piece of his family history and how dare I! So I know that an awful lot of this stuff I'll have to deal with once he's gone.

We too are orphans with no children, nieces or nephews and ends of the line. So I know a lot of this stuff will be meaningless to many. We both have cousins though who have children so will probably pass some stuff down to them. The rest will just have to go.

And yes, looking at photos of people who looked so young and carefree, and knowing ex post how their lives ended, often in such sad and painful ways. It is truly heart wrenching. A labor required of those of us who are the end of the line. Not easy, I know. But there it is.

On the other side though, we've been working at cleaning out over 60 years of accumulation and mess in the barn...while it is dirty nasty work, there is something wonderful about looking at the space that you just cleaned up, all the room you've made, finding treasures you didn't know you had amongst the detritus of accumulation, and that sense of accomplishment at having made a tremendous difference. So there's that too.

I so relate to your stories. I am an only child with a lot of 80+ year old relatives who never had children, so I keep being given more and more stuff that I donâÂÂt know what to do with. I love to be given family photographs and other memorabilia like that, but do I need another china service for 12? Nope. Is that how I need to remember my dearly departed relatives, by keeping a museum of all the stuff that they ever bought? No, not really. But I always found it very hard to part with it all. But what happened over the last year is that we went through a big remodel where we put all of our stuff in storage for months and months, and when we came back to unpack everything, it was like that emotional connection that I had with those things had been broken. I hadnâÂÂt only not missed the stuff when it was packed up, I didnâÂÂt even remember that it existed. I started putting stuff on Ebay (smaller stuff), Craigslist (bigger stuff), bringing stuff to Goodwill (clothes etc.) and itâÂÂs been so, so freeing. I started small, but at this point itâÂÂs like a switch was flipped in my brain. I have gotten rid of like two-thirds of my clothes and honestly itâÂÂs like I have a new wardrobe. I can now find all the clothes that I like, because theyâÂÂre not buried under all the carp that I felt mediocre about but somehow couldnâÂÂt get rid of before. It helps that my husband is on board with the program whereas he too had been holding on to a lot of stuff for no reason. So, to anyone who has a hard time getting rid of stuff or a partner who has a hard time getting rid of stuff, I would say to take heart, that it is possible to get to a point where it gets easier.

Once you come to grips with getting rid of the stuff it is a great feeling when it goes. I'm going through some things at home too. I finally got rid of some dishes and glassware from my mother and grandmother. I donated it to a community garage sale fundraising event for the local childrens hospital. After years of keeping the stuff I finally decided this was a worthy way to get rid of it and hopefully someone wanted it and bought it. I love the open space in my pantry closet every time I go in there now. Also dropped off four bags of clothing and shoes at a local homeless shelter yesterday. And it was great putting three boxes and two bags out for the garbage man from my other project. Also had two bags of paper to recycle and burned boxes and boxes and boxes of cancelled checks. Can't wait to do more.

I even got DH to agree that he will get rid of all the paper copies of HBR, Forbes, etc. that he's kept for years and years. YAY!!