I think I've got the automod correctly configured to assign flairs based on title keywords put in square brackets. I selected no flair for this submission, but as you can see, the automod gave me the "discussion" flair due to the tag in my title.

I don't think it matters whether the keyword is at the beginning, middle, or end of your title. It also appears case-insensitive, but you do have to spell correctly.

Our current list of options are:

discussion

article

media

resource

legal rights

("legal" and "rights" also redirect to "legal rights")

social issues

("social" and "issues" also redirect to "social issues")

intactivism

misandry

progress

education

masculinity

sexuality

("sex" also redirects to "sexuality")

third world

humor

other

And of course, you can also choose your flair manually when submitting a link, rather than using bracketed keywords. Hopefully this will all be of some use to people.