I dunno what the devs were thinking not placing any checkpoints in this area and making you run through the entire level at least twice, and that's assuming you never die, so it's probably significantly more than twice. There's probably some save and quit shenanigans you can use to cut down on the number of trips, but you'd have to plan for that in advance.
I am now a fucking master of this God forsaken level, though.
Edit: Aparently that hellhole has hidden benches???
As someone who is absolutely adoring Silksong being a reality at last. The areas that has this mechanics are legitimately fucking evil incarnate. Holy balls, they're insufferable to navigate.