Just gotta give this a good 
How many of you banging around in that cozy cottage?
Pretty sure he is talking moving down in feet of elevation, not square feet of living space.
Ah. Where is that head smack emoji when you need it?
Probably over on my keyboard where I need it a lot more often than you do 
Keeping it until you are gone (either dead or in a much smaller dwelling) is an option. If you want to make life easier for your executor, you could look into services that will dispose of it when you aren’t using it any more. That could be anything from an auction house to a guy who cleans out houses (or some combination of them.)
I found cleaning out my mom’s stuff sad, but also sentimental. And we (I’m one of 4 siblings) kept a lot of odds and ends. But the real boon was that the realtor who helped us sell the place gave me the name of a guy who made everything go away after we were done with wheat we wanted and what we could sell.
Yes, I think this is what I’m striving toward. I’ll dispose of all the superfluous flotsam and jetsam so that whenever my future path becomes more clear, I’ll be ready to jump – or if things are bad and these decisions must be left to another person, the required effort to clear out and sell will be minimal.
I prefer antiques to newer furniture and have some really special pieces from my great grandparents. An auction house or specialty cleaner could give me an idea of what appeal (if any) they would have and I can either sell ahead or leave them until I’m out of the picture. It breaks my heart to think of my great grandad’s old oak kitchen table or beautifully refinished oak Hoosier cabinet being tossed in a landfill, but if I’m dead, I won’t be able to object. All of it is terribly sentimental, and I’d like to offer it to friends before taking other options.
For now, I’m whittling away at the extra photographs that no one wants or cares about, the detritus that collects in drawers and cabinets and making lists of what can be offered to whom. Just getting a handle on everything is helpful.
Like the old saying goes: How do you eat an elephant? One bite at a time. 
Thanks for the excellent suggestions.
I have several pieces of custom-made furniture. The dining room table that has good legroom and also neatly holds its extra leaves is especially nice. Nice enough that that i took a lot of photos so a different cabinet maker could do something similar when he made the kitchen table, which doubles as a super bridge table.
I also have a living room side table that was my great aunt’s, and was made by her uncle.
I suspect no one will want those when we are done with them. 
At least i know we’ve gotten a lot of use out of them.
We keep boxes because it is a family tradition to hide Christmas presents in boxes to delay the discovery of what they are. So saving boxes all year is a habit. Now, we haven’t had Christmas at our house for seven or eight years, but you never know.
We save rubber bands from the (print) newspaper, but when the bag fills up we bring them to the elementary school across the street where the office staff is happy to get them.
I was born in 1951, but my father’s father, who owned a restaurant, died early and when the Depression hit his mother lost everything. He was in fairly good shape when I was born, but old habits die hard. I remembered him as I was scraping the very last bit out of a nearly empty mayonnaise jar the other day. Wasting food is a sin.
This is so true. Love me an Amazon box.
I worry a bit about that with my dad in his 80s as he lives alone in the 4BR suburban home where I grew up. But he is in good shape mentally and physically and has lots of friends in the area he is active with so it’s not really a concern.
My wife’s elderly family is another matter entirely. Her dad isn’t all there mentally and her mom is getting not all there mentally, severely injured her knee and they ARE out in ruralia
We’re 60 and 58, living in a colonial. The main floor is living room, dining room, and kitchen. Bedrooms and bathroom are upstairs, with laundry and another bathroom in the basement. We can walk in to the basement from the deck/patio outside. I can imagine a time when this won’t work, but my wife’s parents are in their eighties and still living on three levels.
Someone mentioned photographs. That’s another quandary we have. My mom has photo albums with pictures dating back to the 20s. Pictures of my grandparents when they were young, my grandpa as a young soldier in WWII, my mom and her siblings, my parents as young newlyweds, our childhoods, just so many pictures. There has to be close to 75 albums. Then there are also 10 boxes of slides in the trays. We all have our own shelves overloaded with our own photo albums. We have no room. I could never just throw them away, those pictures are our history.
As far as old photos - I got a subscription to My Heritage to build a family tree and the subscription includes enhancement (fixing scratches, etc) and colorizing so I’m scanning and repairing the old photos.
Give the young ones in your family instructions on how and where to re-bury those fossils in scientifically improbable locations. Just think of all the PhD theses you could posthumously inspire!
Good for them. My mid-50s ankle fracture - and difficulties with my wife’s parent’s as they aged, made clear to me the challenges that might present should either of us find stairs difficult. My desire to remain independent is one of the prime motivators in my continuing to exercise. I do not understand how overweight out-of-shape elderly do it!
I am 63 and just had an estate sale that actually turned out to be a decluttering sale. The estate company overpriced my best stuff so high that even on the last day at 50% off no one wanted to touch it. Still I sold $20K worth of junk I didn’t really care to have around. anymore, so good riddance I say. The stuff that didn’t sale I have been putting on Facebook market, I ended up getting more from them there than I would have at the estate sale since they would have taken 50% of the sale price.
I am now awaiting for the estate company to sell a number of small items online. One of which is a Native American arrowhead collection that I knew would not sale for much at my house, but could bring high dollar at an online sale. I also have an ivory netsuke collection, jewelery that was worth more than melt value and numerous other small collectables. We will see how that goes but I anticipate another $10K in sales.
When I do decide to sell the rest I will just have an auction company come and clear out the house. Most likely this fall before I move over to the Philippines.
My Mom left behind about 30 photo albums. After she passed, I took it upon myself to scan the photographs. I used a product called Scanspeeder, which made the process much easier, as I could scan multiple photos at one scan. I found I could finish an album in 90-120 minutes, and I spaced the process out over a 3-4 month period.
I found some treasures that I will keep, and I also found some photos that I determined didn’t need to be scanned.. I copied the end product to USB drives and gave them to my siblings. When I finally discard the albums, I won’t feel much regret.
This is a really useful tip! I’m going to look into it!
I just looked online. The ‘Pro’ version (which you will certainly need) is $39.95.
Ping me if you reach that point! I may be interested in something, depending on the specifics. Of course that’s if we haven’t moved to Canada by then…
If you are serious about just giving a bunch of stuff away, I know a refugee mutual aid org which would be happy to take stuff off your hands if it still exists by that point.