I would think that any options available in game would be allowed to be changed. I don't really see any issue with this because world gen is already part of the timing so any of these setting changes would be timed and recorded as well.

Here is a video with keyviewer. It seemed to me that you need to webshoot very fast to get in the right position. Also, I haven't had any luck doing it indoors, only when the web shoots up off the screen and doesn't grab anything. Doing it indoors should be possible just much harder to get a consistent setup.

I was playing around with this and wasn't able to do it when jumping from the floor but I found that I'm able to get it fairly consistently when I start from one tile higher. I walked to the next screen over and used the first step on the chopper building to jump off of. You need to jump off while shooting a web up and offscreen, while still in the air "stand up" sideways with your back to the floor, then shoot another web "up" relative to the way that you're facing. When done right, Spidey will do his curl animation right as you are hitting the floor and you will clip through.

Hope this helps :)