I'm so glad to hear that. And what a difference geography makes! I just realized while I was reading your story that I've only ever seen one progress Pride flag in real life. I live across the lake from you in a rural area, and Pride flags are very rare here. Progress Pride flags are non-existent, or at least so I thought until a few weeks ago when I drove into a small town for groceries.
I was getting my oil changed in one of those instant-service places, and when I looked out the bay doors, there was a progress Pride flag blowing in the wind. I could barely believe my eyes!
It was flying from the flag pole in front of a United Church of Christ (UCC) church.
I felt a ton of respect for the folks flying that flag, because around here, that's a radical, extremely unpopular act.
I hear you about your doubts about sincerity with some people flying the flag, and if I lived in Chicago I might also wonder about performativity.
Sorry for the not entirely relevant ramble, but I was just struck by how perceptions can differ so much depending on the physical community somebody lives in.