I don’t know if most people read the comments but Laen left this good tip on parting with sentimental objects:
Taking pictures of stuff is also a good way to throw out stuff.
A couple moves ago, I was moving into a tiny apartment with my now-wife, and there wasn’t nearly enough room for all the stuff I had. As I was digging through it, deciding what could go and what would stay, I found that more often than not, the reason I wanted to keep something was because of the memories attached to it. Without the stuff, I might never think of that memory again, and it would be lost to me.
So, for everything like that, I took a picture of the item, printed it out, and wrote a little summary of the memory on the back. The item could then be thrown out without fear of losing the memory.
I like having the physical photo instead of just a digitized copy because it will last much, much longer than the digital copy will. In 50 years, I could dig through a box of stuff and find the photo and get the memory. Not so with the digital file unless someone spends a lot of effort moving files to new media every few years.