When I had a humidor, it was a lot tougher to maintain any kind of order. I kinda knew where everything was because my stash was smaller. I was always pretty careful in the handling of things, so that made it easier.
When I moved to a wineador, I pretty much dedicated drawers to a couple brands... LP in one, Tats and My Fathers in another, etc. I had one drawer for random boutique brands and one for big brands. That kinda thing. The tough part was overflow... if you had a small drawer filled with one catagory, and the drawer above and below filled with another, overflow was a pain in the butt!
Now that I've sold most of my stash, the problem is the sticks rolling around every time I pull a drawer out. I would consolidate them to fewer drawers, but a)I don't want to take the time and energy to move what I have left from drawer to drawer, and b) I'm still holding out hope I'll be able to rebuild the stash at some point and don't want to move them twice!