notspaghetti I only keep things that are still of use to me and am quite happy to get rid of things. I recently sold a lovely 19th century kitchen dresser that belonged to my sister, who died in 1991. I had always loved it and it said so much her taste and her house. 32 years on, we have had an extension built, and the dresser was too tall for the new kitchen, so I sold it. As you say I do have a picture, but that was taken for insurance purposes.
The same with clothes. I kept both my sister's and mother's dressing gowns, they were both fairly new and very warm and each lasted me for years. Ditto my sister had a winter coat I covetted - and kept and wore.
Some things get kept a few years for purely sentimental reasons, and then get donated or sold onwards.
We are lucky that our children are also old furniture people, albeit mid 20th century modern, but I know that they have shed covetuous eyes on some of our house contents. They will take what they want and send the rest to auction, my books will be offered to a specialist bookseller.
But that is what I did with my parents and sisters huse contents. Took what I wanted and disposed of the rest