Tagging 

AWB First off, I use WP:AWB for a lot of this tagging. I'm not sure how familiar you are with it, but here are a couple of simple approaches.
Generate a list from Category (recursive, user defined level)
Choose a small number (two or three)
Convert to talk pages
More->Prepend 
Skip: If exists
Start

Alternately:
Generate a list from Category (recursive)
Filter->Removing all pages not containing "X" (i.e. keep all pages with "Vermont" in the title)
Convert to talk pages
More->Prepend 
Skip: If exists
Start

These methods are neither perfect nor exhaustive, but as you can see, you can get some good work out of it. Let me know if there's more I can do to help you. —❤T☮C☺M☯