Blessed, you are doing a lot of good work.
I think we have to figure out in our minds why things are like they are. Will we not have any memories of things if they are tossed? I believe for the most part we will not forget. But things that are truly not important to us any more, we might move on and not think about any more. And that is good. Room in our homes and brains to live with new and consider new things.
I clean out because it gives me peace, time, and order. Order is very important to me. When I can't find something or if something takes me twice as long as it should I get very anxious and sometimes angry.
My pile of photos to discard are sitting at the end of the counter right by the garbage can. I've not been able to throw them out yet. They are pictures of DH's parents friends, neighbors, people we don't even know, their vacations and homes, etc.
And see that's the thing, our stuff means something to us, it's our memories, our dreams. But after we're gone someone will look at it all and say what is this, why did they keep it? And it'll be tossed. I don't think we forget the things that go out...unless that thing really isn't important. Clearing out stuff leaves room for new spaces and times and new thoughts. That's what I want.