My lead on the Chester Ave job bet me lunch I'd never get the drop through, and he was half right
Had a run on a two story in Chester Ave where the customer wanted the outlet moved to the far wall, and my lead swore the fish tape would never make the turn through that old 90. He said if I pulled it off he'd buy lunch, so I spent 40 minutes feeding a glow rod from the attic side instead of the wall, and it popped out on my third try. What he got right was the part I ignored, the pull string had to be snaked before I cut the box hole or the insulation would eat it. He's been doing this 22 years and was still wrong about the tape, still right about the order. Anybody got a better trick for those tight old bends besides the glow rod and a lot of hope?
I used to roll my eyes at the old guys who said "just use the existing wire as a pull" on these Chester Ave type houses, because on a tight 90 you can't always trust what's in there. Then I watched a guy on a 1920s duplex tie off to the old cloth wire and pull it back through with a new string taped on, and it slid through the bend like it was greased. The catch is you have to check the wire is sound first, because if it snaps inside the wall you just made your day way worse. For tight old bends I'll still reach for the glow rod, but a little dish soap on the tape and a shop vac taped to the far opening to suck a string through has saved me more than once. The vac trick feels like cheating the first time you see it work. Your lead was right about the order though, the box hole cuts first and the insulation eats everything after.