Good questions. Typically the Pride set airs the Friday before the parade, which in the case of this year is next Friday, the 24th. I assume the same will hold true this year. (Which unfortunately means I'll miss the set, as I'll be up in Presque Isle, Maine, for the wedding of my friends Josh and Alli.) As to the transgender songs, I have to say I doubt it, simply because I am literally not aware of any songs that address transgender issues. If one were to hit the mainstream, or even a significant inlet, I'm sure Dave would try and play it, but I don't think there's anything with that level of visibility/recognizability at this point.
Welcome to the Clubhouse, too! Hope you're getting a kick out of it.
Gaz, who runs rap in his free time