So when my Dad passed away, I had his and my step-mother's house in Panama City, Florida (plus 2 rental homes) to deal with. Filled to the brim. That cartoon of 'someday this will all be yours' - yup, that's me. I also now have my step-mother up here in Nebraska (this is where she is from and where she wanted to be). She is now in independent living (probably ready for assisted). She had a house up here, too. The easiest thing I did was to sell one of the FL houses to the tenant. Thank goodness, for that house I did nothing as far as possessions or fixing things or anything. As is - and sold. I tried to do that with his 2nd rental down there, nope, still have it with tenants. And still looking for an honest, reliable, handy man in Panama City, if anyone knows of anyone!
I couldn't get my step-mother to go down and go through things. Over a year later Hurricane Michael hit. Then I had a house full to the brim with stuff with significant damage, a leaky roof, some water came in, etc. So I went down and did not take my step-mother. I will never hear the end of it. Had I taken her, I would still be there. I did bring back things she told me she wanted. I would call and ask - do you want this or that or whatever. As a result, she lives in a 2 bedroom independent living facility. 2nd bedroom is all the boxes I brought back (5 years ago or so now)? Her master bedroom has her bed and then more boxes. She has a few things in a storage locker there. What a shame to have all that clutter. But her choice. And for me, meh, it won't be too hard to get rid of the rest of it. It was an interesting exercise. Not one I would wish on anyone. But because of Michael, anything could go to the curb. Because of Michael I could donate things you wouldn't normally be able to. Yup hoarders (that is where I get it). My step-mother sold Avon and had some very nice lotions and such that I was able to donate and I'm sure were appreciated by the recipients. We replaced the carpet and I took some of the old carpet to someone living in a tent in someone's backyard. Michael provided some unique opportunities. And extremely, extremely, lucky to have a brother-in-law that is a handyman. He went to FL for 2 months and basically flipped the house for me - but did an amazing job - cares about doing things right. The house sold (by owner) immediately (I wanted to try one weekend before listing it). I was very fortunate. That and 4 siblings - we all went down for a week. One brother went multiple times with me. He has a camper we could stay in after the hurricane. I had a lot of help.
So as my father's keeper, so to speak, I have sold a car, a van, a camper, 3 houses, and still have a rental and a step-mother to deal with

Oh, and timeshares, I have timeshares now. That's why I am here
My mother is in a memory care unit (in Massachusetts). She was incredibly organized. She had gone through, and given us, things she thought we'd want ( can't say I do but... letters I wrote here when in college, etc). Still everything has been gone thorough as part of her moving process. My sisters probably overly careful, but tried really hard to be sure things went to people that wanted them or they should go to, etc, My brother's little wicker rocking chair is stored at my sisters. Everyone agrees it should go to him. I am sure it never will. He lives in California. His grandkids (out there) are now 4 and 7. He's been home multiple times and hasn't taken it yet. He did take a 'recreation' picture of his grand-daughter in it just like a picture of him he has.
@Cornell , I know what you mean about dividing things up while someone is still present. First, sorry to hear about your mother. Awkward, hard, and everything in between. Somethings I told my Mom what I was taking (very few, but for example she needlepointed 'a boy, a girl, and an angel' hummel picture and everyone agreed it was meant for my daughter - I wanted her to know my daughter had it), other things I have stored and will give to my kids after she passes. Very very weird feelings on the overall process. My mother has to give 30 days notice, even when she passes. I guess we'll be thankful when the time comes. Clearing out in just a few days would be hard and harsh (and would, once again, place most of the burden on my local sisters).
All in all - came back from visits to FL and MA resolved to clean up after myself (and I have yet to do so - shame shame on me).