Thanks for posting this Brian. I like "101" posts. Makes me not feel like an idiot for my OCD tool box organization habits. I typically redo my box(s) a couple times a year each time removing things I never use and placing these items in my "never use" box in the corner and then give stuff away out of this box when I realize I never touch it... I have also realized that I have a compulsive habit of purchasing a tool for a one time use when I should have just borrowed it. It took me a long time to realize this, I now hold off buying until I have borrowed a certain tool a few times.
Last time I went through my boxes I came up with two "extra" drawers of which I now feel I need to fill up... Before this I was shopping for a new cart because I thought I was totally out of space.