alt Hacker NewsI have a similar system but it's a bit more ongoing.
Since March 2018 I've created a new playlist "[Month Year]" on the 1st of every month, and every time I listen to a song I enjoy (whether it's new or old or whatever - no rules) I add it to that month's playlist. In fact the only "rule" is to never remove a song once it's added.
Then at the end of the year I make 24-song a "Best of [Year]" playlist where I go back and pick 2 songs from each month, in no particular order, to sum up my year in music.
This tends to reflect my music enjoyment (vs listening) much better than Spotify Wrapped, which over-indexes on music I listen to at work or in the car (when I'm often not really paying attention).
I just crossed 100 months back in November or December, and I have to say it's pretty fun to go back and check out a given month/year in the past (much like the author) and revisit what I was into at the time.
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I have one playlist I add songs to I listen to on repeat. Going back through it, it really shows what I was mostly listening to at what time.
This is a really simple yet clever system and I may have to give it a try! I've created vibes-based playlists at points-in-time but otherwise just dump everything to my "like" list on Spotify which is fairly poorly organized after so many years.