It's criminal how little attention Trish Hidge and Pamela Winchell have gotten! Especially when there are fans willing to come up with so many elaborate ideas and fics about characters who are literally only mentioned in one or two lines in canon. So here, have a bunch of my thoughts on the characters, and hopefully it'll kickstart some other people's imaginations.
Trish is defensive of the former Mayor, looks up to her, respects her, and tries to emulate her in various ways (although her skills aren't nearly as polished as Winchell's are). Could just be that Trish respects the office -- we haven't heard from her since Mayor Cardinal was elected -- but obviously the more fun option is that she's devoted to Winchell personally. Loyalty kink! Mentor-and-devoted-subordinate dynamics! Imagine Winchell acting exasperated when it always takes Trish five minutes to finish turning into a horse, but not-so-secretly thinking it's adorable.
And yeah, it's canon (if you take Trish at her word, at least) that they can both turn into horses. And fly. And turn invisible. Think of the possibilities. Sex in midair! Turning invisible to have schmoopy romantic moments without worrying that Leann Hart will have photos on the front page tomorrow morning! Imagine Winchell being in a really boring meeting, until an invisible Trish sneaks in and starts whispering sweet nothings in her ear. Alternately, Trish goes all-out and starts doing a striptease. Winchell can't see it any more than the rest of the room can, but the difference is that Winchell knows it's happening. Any time she seems more eager than usual to get away from the council, it means an invisible Trish is going to get tackled in the nearest bathroom within two minutes of the close of the session.
It's also canon that Winchell grows different kinds of moss -- possibly for some esoteric Night Vale purpose, possibly just as a hobby. Imagine how excited Trish was, assuming she was being offered a really weird come-on, the first time Winchell suggested "come over to my place and let me show you how to stimulate my moss patch."
My mental image of Winchell looks amazing in expensive tailored pantsuits, and wears a lot of classy bloodstone jewelry. That said, she looks impressive in anything, clay-stained smocks included. Attitude is everything. Trish wears cheaper imitations of the same outfits, and is a lot more excitable, but she's constantly getting better at carrying herself in that striking way.
(The only definite appearance info we have on either one is that Winchell has olive skin. The way I draw them, Winchell looks like she could be Eleanor Holmes Norton's younger sister -- same skin and hair tones, same imposing sense of presence. Trish, meanwhile, is like a bootleg version of Huma Abedin: way more excitable and less poised, but looks remarkably glamorous when she's holding still and not talking.)
One of Winchell's long and possibly-metaphorical speeches referred to the Mayor as having six arms. If she was, in fact, being literal...just imagine her using all six hands to reduce Trish to a wonderfully overstimulated puddle of sensation. (Also possibly literal. I want lots of weird!sex fic here, beyond the fandom standards like tentacles, is what I'm saying.)
Then imagine Trish's reaction to the recent election. Imagine her putting her well-exercised denial skills into practice harder than she ever has before. Imagine her ultimately being even more upset about it than Winchell is, and being the one who needs to be the recipient of comfort sex.
...Imagine Trish being furiously angry with Mayor Cardinal's existence for months afterward, until Winchell is all "you know, you're going to need to come around and respect the new holder of the office eventually." And, long story short, it gets solved with a reconciliatory threesome.
tl;dr TRISH HIDGE/PAMELA WINCHELL. Get on this, fandom.