Cool stories guys, I cant say I have much that is old, as I have sold EVERYTHING I used to collect, and have started over on a very limited basis.....the TTM/IP bug I had for my first 25 years turned into the "lets see what I can get for this" bug in the last 8! It has been fun though! I have donated a lot too, our dear friend who Baptized Ellie (2012)and myself (1981) and married Laura and I (2006) is a Priest on the North Side of Chicago, and we have given him a lot for his parish fundraisers.
So in answer to your question, Brian, I dont really have anything from my childhood, though I will say that those items sent our family on 3 vacations, one to Europe, one to Colorado, and one to Missouri (Johnson's Shut Ins/Elephant Rock state park: Ellie's first vacation in our camper last summer!). Those memories are what I cherish, I never look back at what I sold (lots of entertainers, many now dead: Dean Martin, Anthony Quinn, etc.) Honestly, I do think that I probably got more out of them financially than I had ever invested, and the memories last forever!
Now that I have told you my life story and philosophies on collecting and selling (!!) my oldest item is probably from 2005, when we met Bruce Weber when he was head coach at Illinois, he was recruiting during his Final Four season, and he very kindly signed for us, also got Roger Powell Jr. that season too, our favorite Illini player, which was awesome!
God Bless,
Kevin Mc