I'm a boomer too so agree with some of what you said, for a long time I stopped listening to music after the early 70s, it's natural to like music of the period you grew up in, will Millennials like the music of 2050?
Having said that, I'm really starting to enjoy contemporary music, it helps to know people of that generation and how the music reflects their period. Grew to like Courtney Barnett, love Billie Eilish, a more obscure artist (Fawn Segerson). Some of these are a little retro style, others rather cutting edge. Eilish is resetting the standard to a pretty high level, she is no Justin Beiber and is incredibly versatile.
You see a lot of contestants who are incredible on talent shows and then the work gets over produced, the rough edges filed away and all these embellishments are added.
Janis Joplin, Bob Dylan, Ringo Starr, all terrible singers, Ringo was an average drummer. However they are extremely original in many ways, today a lot of the vocalists are technically great but the performances are formulaic. It's like there are a bunch of check boxes to fill:
Soaring vocals to demonstrate raw power
Vibrato to show your amazing control
Alternating between breathy lows and highs
Demonstrating your range
It's hard to figure out what is an honest performance, music in the 50's was manufactured as well with all the boy bands and boy crooners. Then in the 60's all the rules were broken, you didn't have to gyrate to get fans and it was much more focused on the music.