Shonda, I struggle with what/how much to keep of our children's items. I have kept a few sentimental items - things they wore home (we had hospital births) and some cute clothes they wore a good bit. I also admit to keeping (to his future embarrassment, I'm sure) some of DS's first "big boy" underwear. They're just so adorable! I thought of taking the digital photos, but then the process just became so overwhelming. My family tends to overbuy by a tremendous amount, so we have lots of clothes, and they didn't even wear all of them!
So part of me hates just to give all of that up, but OTOH, I feel that I want to remember DC and the things they did, not the afternoons I spent tearfully taking pictures. I read once in a book on simplicity that many people spend more time preserving memories than making them. One group of DH's family is like that. They told us that they have 3500(!) pictures from a 12-hour labor & delivery. How could Dad have been really "in" the process at all? He was taking pictures constantly! They're extreme (I hope), but I don't want to be like that. I watch them, and so much of their lives are staged. I don't believe I've seen candid shots of them; they go to elaborate lengths to make everything *look* as if they were having fun. The end resul (from my perspective) is that personality is lost in all of the memory-capturing.
I also - to add to the emotional side of this - had my house burn down when I was 8. Most of my baby pictures and reels of film (ah, the old days) are gone now. I think that snapped much of my sentimentality away - or at least makes me fearful when I think of it. Though I didn't care so much about baby pictures at 8, I did care about other things in the house, especially trophies I'd won.
Anyway, we are definitely doing the 5 things a day challenge, and we're going to try to get rid of 2,010 items in 2010. I figure either we'll get rid of tons, or our entire house will be clutter-free.