Here is a run through Kaboom Quarry without losing the double jump hat.

I do the skip in a few places. Fastest run is at the end.

I think this is viable for Any% and All Stars.

wow, just tried it. must say the second jump (where you usually grab the football upgrade) is pretty hard and definitely a runkiller :D routed that far aswell, but couldnt get up there, so i prefered to grab the football upgrade instead, cause you get the flying upgrade in the level afterwards back anyways

Yeah, it's really tricky. Works well if you are doing a single level run. But probably not worth it in a longer run.