Great stories. I likewise grew up in/around Philly. Never made it to the Gilded Cage, but would cut school to public trans my way out to the Main Point https://en.wikipedia.org/wiki/The_Main_Point in Bryn Mawr. Caught some great shows there.

~ Steeleye Span on tour promoting their Parcel of Rogues album; at the end of the show they set down their instruments, walked past the mics to the front of the stage and delivered the title song acapella. Gave me chills.
~ Fingerstyle monster Paul Geremia opening for Jerry Jeff Walker.
~ Bonnie Raitt, Ramblin Jack Elliot,..

Of course the downside of growing up in Philly is that you become a cultural imperialist about cheesesteaks, hoagies, grinders, pizza, pretzels, water (wooder) ice,...