When I was in my early 20’s I lived in a drafty dump with 6 other dudes. It was a really bad winter and after an insane December heating bill, we turned the heat down to the low 40’s. We wore hats and gloves inside. I slept in my Carhartts.
So yeah, that’s a thing young broke Midwestern guys are known to do.
I never took Skyway to be from the perspective of a homeless person, but rather a low wage maintenance type worker (a janitor perhaps, like Paul was) who walked a stretch of it in his daily commute.
This song will always remind me of when my wife were going through IVF. The Mayo Clinic is about an hour south of Minneapolis (an hour north of us) and uses a lot of skyways to connect parking ramps where we’d park for the appointments to the clinic facilities. We were hopelessly pining for kids, not unlike the way the narrator hopelessly pines for the object of his affection. We just put our 13 month old daughter to bed. She spend the past 15 minutes falling asleep in my arms.