Things are making a lot more sense. I did misunderstand the $variable. It makes sense how it counts words.
on *:TEXT:& just enlisted for & months:#djquad:{
In your example, you are using ampersand incorrectly. That field should use wildcards ? as a single character and asterisk as 1-or-more characters. "*enlisted for ?? months*" would only match when the word before 'months' has 2 digits.
The ampersand seems to work whether it's 2 or 20 months.
I'm not treating it as a number, just a word. If I were treating it as a number, I'd use isnum 1-99 instead of just isnum right?