Crack, nice details on your setup.

I don't have a lot of details to add, but I would say that I try to keep similar items together.  I put all of my sleep system (tarp, quilt, sleeping mat, down booties, insulated vest, and insulated hat in my front handlebar bag.  It may not be the best distribution of weight, but at least I know where my sleep gear is located.  In the past, I have put items (clothes for example) in various locations but I could never remember where each piece was located.