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Is there a music buff's roadmap, some sort of a chronologically-ordered list of the best and most influential albums that gives a coherent picture of how music evolved over the 20th century? And is that a right approach to becoming a music buff? If not, what is?
the key is to put in the listening hours.
how you start doesn't matter much. maybe wikipedia + youtube?
Can you share what your diagnosis is?
While I feel like I've been doing a fairly good job of keeping up with music for the last decade, their knowledge of music, even from before they were born, is extensive and got me interested in exploring stuff that came out before I really cared about music.
Bandcamp is a great place for music artists. Here a huge chunk of the profits go direct to the artists, so it's got every possible kind of music from nobody you've ever heard of.
They have a weekly radio show called The Bandcamp Weekly. It's super varied but they're friendly and they often do themes each week. Give it a go
In parallel, learning music is best when you're having fun. You should start with your favorite artists and dive deeper into their discography. Research the label they were on (fruitful if the label is independent). Look into their contemporaries. Who were those artists? Maybe they were associated with a larger movement/scene, and so on.
Finally, listen to more music! Everything (almost) is on Youtube or Spotify. Make it a point to listen to music everyday.
Given your list I would suppose maybe you like things with a complex narrative, or as is the case for me - music with clever/complex lyrics.
So you could look for music that has a complex narrative, but obviously that helps you find music best suited for you and not helping you build an understanding of what is appealing about music or what makes for 'good' music artistically speaking.
Although maybe you can jump from music appealing to you to a broader feeling for music in general.
Is there some music or musicians you find more appealing than others?