I've got nametapes from when my grandmother was at school and even one belonging to her mother. I could not throw these away. Keep just a few, not all of them. I know exactly what you mean though, it's the dismantling of a life that hurts.
It upsets me afresh each time I dispose of things no longer needed at my mum's house. Each time it's another change away from how she arranged her possessions and it feels somehow disrespectful. Her built in wardrobe now looks like a CH store cupboard with stacks of supplies for all her personal care needs. It hurt me to clear out her clothes and recommission the storage, even though it is a practical necessity. It hurt me to throw away her knickers - she will never need them again.
I sometimes imagine my father returning to see all the changes and wonder what he would think. It took me a long time to be able to box up his remaining things and we still have half his books on display in the carer's bedroom. It is a specialised collection of history books, reflecting his life, but of no interest to carers and just takes up useful storage space. It's been 7 years since Daddy died. This summer those books will get packed, but it will make me cry. It will no longer be his home. If I can't see his things then I will feel more alone in looking after my mum, because I will have put him in the past.