I suppose from the outside some of my posts might seem a bit like a pure math proof, insofar as when you look at a proof in a math textbook, you can readily follow along and see how each step follows from the previous one, but unless you have a background in the area of math, you don't know how the steps were chosen in the first place.
I do some research for almost all of my posts on this forum (even if I think I already know the answer, I still make sure I'm right), but it's a nuanced form of research, guided and informed by a significant amount of background knowledge.
I can give an analogy that I think both of the earlier posters in this thread will appreciate. If I asked either of you, "On Linux, how does the /dev/random special file generate random numbers?", you might not know the answer, but you would know how to find the answer. You would open up the Linux source code and use standard text search tools (such as grep) to find anything relevant to /dev/random, and then, once you found something that looks relevant, you would know how to read the C code and how to follow the chain of function calls and data structures and reduce it all down to an English answer to the original question. Being able to figure out the properties of a complex computer program without advance familiarity with it is probably one of the most important skills in software engineering, and somebody who isn't familiar with that field wouldn't know what steps to follow to do that research, and even after reading those steps earlier in this paragraph, they wouldn't have any idea how to actually implement those steps, without the relevant background knowledge.
So, my point is that if you want to replicate the research I do to write these posts, you are going to need some background knowledge. Unfortunately, the amount of background knowledge required to be proficient at legal research is pretty substantial. I say "unfortunately" because it would be ideal for everybody to be able to determine with relative ease, on their own, what their rights and obligations are in our society. However, the way the law actually works is that you need a broad base of fundamentals before you can really do legal research effectively. Those fundamentals are basically what are taught in a typical US/Canada law school program, such as property law, contract law, torts, constitutional law, administrative law, agency law, principles of statutory interpretation, and a variety of other things.
The way most people today acquire this background knowledge is to attend law school, but if you want to learn through self-study, you'd probably want to cover the same material as a law school curriculum. You'd want to read a large number of court opinions, which helps you become familiar with how it all comes together in practice. Each opinion references other ones, so you can go down the rabbit hole by following the cites "all the way down" and learn a lot along the way. That said, this post is not an attempt to outline a self-study program for legal research. I'm just saying there's a lot to learn.
I know this doesn't exactly answer the question of how I choose what to cite, but I guess the point I'm making is that there isn't a simply stated answer to that, because my methodology is based on having relevant background knowledge. I hope this explanation helps.