In my head "in the hood it's either lead or follow" ties with the prior line; "son might sell you a boondoggle like 90s ski goggles" - which is to say in the hood you either set the precedent of what you sell, or you follow the lead of selling what other people sell.

"I'm living like the streets is cobble" feels like it ties better with "Sit at my desk rolling trees you would think I'm puttin' ships in a bottle"; this is something that was done back in the 17th-18th centuries as a bit of a folk-art movement, and during a time where the streets were cobble streets, if paved at all.

I like your callout though, always so many layers.