i agree with a lot of what you are saying Reine...i think there is very little to be done about it, and i don't think the anecdote about your son translates to any big meta trend.
reaching people is hard...transsexuality is very difficult to understand....what ts people want is hard to get... many of us would prefer more dress down casual days for caitlyn...
nobody can be all things to all people.... caitlyn can't have it every way...her platform IS the k-clan... its true that its hard to take people in that circle seriously sometimes but thats the bargain...perhaps caitlyn can pull away...the ratings were so so, which means this can likely fade anyway.
i have two daughters ..they have their buddies and i see a lot of them...
in their circle they don't laugh at us...they are anti racist, anti phobic...etc...they and their friends are very serious about it...they stop being friends over this stuff
rightly or wrongly they would be in your son's face if he made that joke to them!!!! or joked about race or gender or anything that hurt others
however
..i don't think either your son or my kids represent anything but themselves and perhaps their friends...