Hey @Ser_Dirtnap,
This one doesn't require anything fancy – just a good understanding of Keyboard Maestro's capabilities.
Keep on plugging away, and you'll improve your specific knowledge and your ability to find what you need in the Keyboard Maestro Editor, on the KM forum and in the KM Wiki.
Take a peek at this post for some hints about finding help:
Frustrated w KM and KM Forum - Maybe I'm Missing Something - #6 by ccstone
Here's an example of what you're trying to do:
Check for Punctuation Character v1.00.kmmacros (6.4 KB)
Display-Macro-Image
-Chris