I'm very glad you have the email @Dimity and can take ideas from it for yourself.
There is a mourning process for the loss of all of those past experiences, especially when you've put so much of yourself into them - they are so much more than even the sum of their parts, aren't they.
Digital seems like such a good idea, but becomes outdated so very quickly as you say, they were meant to last forever, but didn't.
I really think it's the emotional attachments that slow us down from decluttering. We think we might forget about those parts of our lives, and we might do too, but for me, there's been a lessening of overall stress from making the efforts (and it IS effort) to screen and sort and cull stuff.
One other thing I want to mention - do not cull when you are angry or really depressed - in the past I tossed things in a temper that later I realised I wished I hadn't, and when I was a teenager, my mother burned some special to me things a couple of times when she was angry with me under the pretext of 'cleaning up'.
When you can, use, recycle, reinvest ways to use - stuff and things so you're not spending money you don't need to.
even with food, I have a whole pile of Melba Toast packets I bought for some reason and don't snack on anymore, so have been making an eggy cheesy pan bread with them to use them up.
Get creative, have some fun trying different ideas.
