Interesting thread.
I think that for many people, and I am one, music is "the soundtrack of our lives."
As my life circumstances and outlook change, so does my preferred soundtrack. More jazz these days.
In college, I was all about Steely Dan and what is now called "yacht rock," then found that punk and post-punk spoke to me a lot more directly.
Cultural context has always been a factor in music tastes; younger people, especially, use it as tribal identification. Are you a hesher, geek, skater, popular kid, jock, cheerleader, intellectual, art weirdo, gay, etc.
This carried on in a larger sense as I got older; I was very dissatisfied with the mainstream political and cultural environment in the United States in the '80's, so I recoiled from anything that seemed to support the status quo, and embraced music that I perceived as subversive.
With that context removed or dissipated, I find that I can go back and appreciate music that at the time I wrote off as reactionary or passive. I've seen it happen with people who were on the "other side" back then; at the time they thought that punk and new wave were total crap, music for idiot degenerates but 30 years on, can appreciate it.
Of course, pretty much everything that was once scary and transgressive will eventually become cuddly. I was at Red Robin last night and I am pretty sure that I heard The Misfits on the piped-in music.
As far as finding new things to like, I still do it, although not as much. I rely on radio, either my local college station, or curated Internet radio stations. I mention "curated," because part of the fun of radio for me is hearing what an actual person thinks is a good flow. I have friends who really like Pandora, but I am resistant to having an algorithm feed me tunes.
I discovered Brant Bjork via one of my favorite stations, Turn Me on Dead Man, which is dedicated to vintage and modern psychedelic music.