Its so so hard to get rid of all the things that you have mentioned, but, its very freeing big time. My Mum died 13 years ago,she was 86. but for the previous two years before her death, she began to start getting rid of things in her home, saying that she didn't want to leave a load of stuff for others to sort out when she was gone.(she had also organised , and payed for her own funeral) and given me the undertakers receipt !
To be honest, my Mum was very very organised, and did a brilliant job sorting her things out, so much so, that when I had to go and sort her flat out after she died, ( I had to drive miles to her place to do so,as my sister who lived near to her, refused to help in any way, as they had fallen out years before., and sister refused to attend Mum's funeral also.
I have kept only a few small things from Mum's. mostly her many photo albums from over the years.
But the point of me saying all this, is that I am now myself doing exactly the same, I am over seventy now, still in good health etc, but I want, and do so, keep clearing things out most weeks. and even if I live till I am 100, omg, I will be super organised !
I have given my son and daughter,, both 40 ish in age, all the things I have saved of their's, like their cards sent to me, their school and Uni reports, and early chlldhood medical papers etc, They will not be wanting any of my type of reading books, nor any of the pictures on my walls, and definitely not my small collection of duck ornaments ha ha. (they might like my houseplants though !!)
I do know how very attached to things that most people can be, I have been the same for years and years, but now I need to be organised like my late Mum was, especially as she always thought I was never organised at all ha ha.