If you are the best in the room, you're in the wrong room

Theoretically someone will always be the best in the room so this sounds like a recursive problem with no solution if everyone is scrambling out of the room they find themselves to be the best in XP

_{I am aware that I both take everything too literally and overanalyse everything too excessively}

trying to shadow people that I want to emulate

I did this with my boss when I first started working. After my shifts I would jump into her class and quietly follow her around and ask her questions when she wasn't directly busy with the students (her groups are at an age/level where she can sometimes sit back a bit and watch them from far enough away to be able to make sure they're doing the correct things rather than having to be directly under/next to them to be able to catch them if they screw something up). It was incredibly useful and I learned a lot and I only do it every so often now and have many new "stupid" questions for her.

One of the best learning methods out there I think, and usefulness increases immeasurably if the person you're shadowing also happens to have teaching styles compatible with your learning ones.

_{I lucked out, my boss knows how to deal with brain glitches}

I don't think there's anything wrong with the guidelines but guidelines shouldn't make an intelligent individual be prisoners to it

A guideline is a direction you should go in not a script you need to prescribe to verbatim. You (and the seniors before you that you were emulating) did exactly what you were supposed to do with it (model your interview/questions on the guideline but ask/carry it out in a way that works for you to be able to get the answers that you need to be able to do your thing).

then that's the time I've probably outgrown an area and try to seek another area to get better at

Definitely a way to do things if you're getting bored. Another thing you can do is be the mentor for others walking a similar path to you.

The "street smart" attitudes always have a practical use. In my limited experience much more useful than just knowing how to look up an answer in a book and being completely confused because there's conflicting answers and all or none of them are right to some value of right (which I feel is where a lot of the world's problems are).