Bump into this a lot of times for large category lists. When the number gets more than 30-40, it is really a hassle to manage. And the ui is very very easy to screw up (I think there are some subtle bugs).
I make it a practice of always putting a category into the right order as soon as it is created. Doing it in bulk afterwards is a lot of pain and risks. But of course @pfaffman is bulk loading an entire site so this won’t work for him.
At lesst being able to move a parent category as a single block wirh its children in the sorting will solve most of the usage prob.
Thus: Recorder a leaf category: Just move up/down. Doesn’t go out of parent boundary.
Recorder a parent category: The whole tree moves up/down preserving children order.