Really, I think the best resource for coming to a better appreciation of pop music (or whatever other genre you want to appreciate better) is spending time talking to and interacting with pop musicians, songwriters, producers, etc.
The more academic approach you're wanting to make won't work near as well, in my opinion. And I say that as someone who has degrees in philosophy where aesthetics was one of my areas of concentration. --But I have degrees in music theory/composition, too, and I've made my living as a musician, composer/songwriter and arranger, often working in genres that are considered "low art" by folks who make such a(n in my opinion nonsensical) distinction.
Get to know some people who are making pop music because it's what they want to make, preferably via some people who aren't just starting out (although of course it's difficult to have access to famous folks, but it's better if you can talk to people who are relatively seasoned). Spend time talking about music with them--why they love pop, how they feel it reflects their craftsmanship as a musician and songwriter, spend some time listening to music with them, etc.
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