I'm stuck in a similar boat with the cards, Scott. Right now, I have a lot of baseball, football, and basketball cards sitting in a trunk in my grandparents' attic because I simply got sick of looking at them. It's one of those "fad collections" that I got into around 1987-1990 (when comic books weren't cool and I was obsessed with being cool) and although I've got some neat stuff by other people's standards, I just don't want it anymore.
It got to a point where my mother was asking me about them and I said that I relinquished all ownership rights of my cards to her and my father, and they could do with them what they wished. For a while I thought, "Well, I do have Barry Bonds, Mark McGwire, Sammy Sosa, Barry Sanders, etc's rookie cards, so those must be worth something", but now I don't even care enough to look and see what they're worth. I also had the first SLU Michael Jordan carded for some bizarre reason, as I don't remember ever actually buying it, and if I didn't open it, I must have not been terribly interested in it to begin with.
The only sports memorabilia item that I would want to keep has gone missing (a personally autographed 8x10 of Wayne Gretzky), so the rest of the stuff is as worthless to me as it is on a financial level right now.
And I've found (especially with magazines or toys) that if you aren't sure of whether to toss or keep something, you can always donate it to charity. The sports card thing wouldn't work in this situation, but magazines/comics/etc would be great for schools or children's homes, and even the old hats could go to Goodwill or the Salvation Army. Always remember that our trash could be the greatest thing in the world to someone who doesn't have anything.
I'm actually fairly ruthless with stuff I don't want/need/care about, but I'm lucky in that I never really regret getting rid of it. I think that a lot more of the stuff I've given to charity or sold would have gone straight in the garbage if it hadn't been for second thoughts.
My wife sees my old sports cards, comics, MOTU/GI Joe/Childhood Toys, and says "sell them or chuck 'em".
I have yet to meet a woman who doesn't feel this way toward collectible stuff, but the moment you mention throwing out some of their old clothing or giving it to charity, they freak the hell out. "I might need that dress I wore when I was 12 years old at some point!" Or, the more often used, "I wore that dress on my second date with you in 1979 and I can't give that up!"
It's all about the attachment factor, men or women. Women go absolutely ape**** when I tell them that I don't have any pictures of anyone PERIOD in my home, and men tend to think that it's a bit strange as well.