If everything goes according to plan...and the puzzle pieces are coming together...my wife and I will be moving to a new home in a month.
I don't think I need to save all my school papers. The collection of newspaper articles I wrote for a college newspaper, and a collection of English papers from my Senior year in high school should be sufficient. I don't want anyone reading anything earlier than that anyway. Except, perhaps, a poem I wrote when I was six, but since I scanned in the crumbling pages, I don't really need to save the original. (My handwriting has improved, a little, but not my artistic skills.)
I do wish I had a copy of several letters I've written over the years, but alas, that is the way things are with letters. The sender doesn't usually retain a copy. That is an advantage with email - if one doesn't delete them.
The photograph of some pigs I took at summer camp when I was 14 can be pitched, along with several other similar photographs. I'll try to follow the Practical Archivist's advice on what to keep, and what to toss.