I will throw in my thoughts on what I look for in a boot beyond just fit:
1. The boot must not look like a waffle, it needs to be primarily made from a single piece of leather for a somewhat rigid fit.
2. I like an aggressive tread, that isn't too soft. Soft means that it will be slipping and sliding all over the place. Too hard of a sole will be even worse.
3. The lacing system must hold the strings tight. This may sound trivial but I have had brush that will pull on the laces and take them right off the hooks.
What do you guys look for?