I was wondering if you had [...] advice on the path of markets an aspiring short-story writer should/could take?
As I said in response to the comment, that's an excellent question. It's also a difficult question, with no easy or canonical answer.
In simplest terms, no two people are going to find precisely the same path. It depends a great deal on what you write, what your audience is (or is likely to be), what your career goals are, and even nuances such as what length you write at.
The conventional wisdom, which I largely agree with, is to start at the top markets and work your way down. What the conventional wisdom doesn't handily define is "top markets." For example, Analog is the highest circulation market among the digests, and widely considered one of the top short fiction markets in our field. However, if you're writing highly surreal erotic elfpunk in a nonlinear stream-of-consciousness structure, the good Dr. Schmidt may not be your most natural reader.
The logic still holds water, though to apply it effectively requires a good understanding of both the markets in the field, and how your own work reads. Neither of these understandings comes naturally. The above example is extreme, but there are certainly far more subtle cases.
(I'm going to speak out of both sides of my mouth for a moment and note that I once sold a science fiction story to Black Gate, which specializes in high fantasy. Likewise, Tobias Buckell has sold at least one fantasy to Analog. So even the above only applies largely, not exclusively. The basis of such exceptions, rare as they may be, is that story trumps all. An editor will buy a good enough story, even far outside guidelines. Don't count on this, though.)
You might define top markets in terms of any of the examples I gave in the prior post. That depends on your career goals. If "make a living at this" is key to you, aim for highest print runs and pay rates, for example. Baen's Universe has the highest stated pay rate of any regular periodical market out there. Analog has a wider readership. Which is more important to you?
Likewise length. Check guidelines. While there's almost always some bend in guidelines, you're not going to shoehorn a novella into Realms of Fantasy, which has pretty strict upper length limitations, probably for production reasons. Some of the really interesting literary/slipstream markets, such as Flytrap and Lady Churchill's Rosebud Wristlet, favor pieces at quite economical lengths.
Look at this another way, now. if "make a splash in the field" is important to you, what markets are regularly reviewed, regularly generate award nominated stories, YB stories and honorable mentions, and so forth? Polyphony has been up for a WFA three years running, we produced several WFA nominees and one winner, as well as a story which landed in Best American Short Stories. Nice company to be in, if that's where you'd like to be seen.
The answer to the question boils down to "it depends." The best way to think about it may be to simply define where you want to be, who you want to be seen with on a ToC, etc. This is my "bellwether" writer concept I mentioned in the previous post. Like Ray Vukcevich's work? Look at the markets he's been in. Think matociquala is a killer writer? Follow her into her marekts. (It does help to tag onto writers with active short fiction careers.)
In the end, as I stated above, good writing trumps everything.