fun idea for sure, but i think it’s underrating the fundamental misanthropy that undergirds the show. given how deeply cruel the characters can be at times, it’s hard to imagine a trans plot being played compassionately here.
that said, we can work with this. instead: jerry cynically changes the sex marker on his documents in order to pay less for car insurance. as for the dress plot beat, elaine (who is established within the text of the show as a horrible driver) does not want to accept that women are being charged less for car insurance and retaliates against jerry for this, giving him the dress as a provocation. sort of an “if you want to talk the talk, you need to walk the walk”. not really sure what george would be doing in this episode aside from reacting in confusion. we can figure that one out later.
the c plot with kramer and newman involves them ducking into a gay bar because it’s pouring rain or whatever. they do not realize it is a gay establishment. within minutes, the guys there buy them drinks because they look like they are an invented-for-the-show category of gay guy that everyone there happens to be into. kramer is a giraffe. newman is a walrus. i’m open to suggestions with the nomenclature on this one. as a result of this, they keep going back and end up ensconced in gay bar social scene politics until they eventually realize that this is a gay bar, realize that they should probably not be involved in whatever is happening, and leave never to come back.
perhaps jerry could not make seinfeld today, but i suggest he leave the royal you out of it.