I was distracted today, and now I feel a little sick. (If my sense of smell goes away, I'll mention it. Right now, it's extremely present.)
Point is, I got just a little work done researching how pip works. What I concluded is, there doesn't seem to be much documentation (at least, on what I want to know) anywhere obvious, so to make progress, I'm going to have to formulate a bunch of basic questions, then work on answering them, and possibly write stuff up to flesh out the documentation.
I'll hopefully make progress there by the end of the week. Right now, I just want to work on not feeling gross.