I think that a lot of the music I enjoyed as a teen and young adult was heard on inferior equipment. I enjoyed it and I got used to the way it sounded on that equipment. I remember that A Ertegun said he did the final mix of Aretha Franklin's music over car stereo speakers. I still think that Bell Bottom Blues sounded the best over an old Dynakit tube amp through AR speakers and a Garrard turntable. Most of the old rock and roll I play on my system doesn't sound as good as I remember. That may be my system, not enough power in my Pass Aleph 5 for my Talon speakers, but I think it is my memory and the way I heard the music first.
I do own around 1000 CDs. However, I usually try out CDs when I find them at a Half Price Bookstore (especially their sale rack at 1.00 or 3.99). There are a few artists which I will pay the full price for Richard Thompson, Chris Smither, Rosanne Cash, Johnny Cash, Tom Waits, Delbert McClinton, Buddy Miller, Karrin Allyson,Scott Hamilton ... Recently, I found both Greg Trooper albums for 3.99 at Half Price and I have added him to my list. I think you can get a good music collection if you are patient and shop.
My son listens to Rockabilly and I actually think there are a lot of good Rockabilly players like Southern Culture on the Skids, etc.... I find that there is a lot of good music out there for youth to enjoy and for old folks like me. I think I just enjoy folk, jazz, and alternative country more that I enjoy rock and roll anymore. Some of the more thoughtful rock and roll, Bruce Springsteen, John Hiatt, Van Morrison, Billy Joe Shaver, etc., still sound good on my stereo.
I agree that most big time music is more about entertainment than the music. This is probably the result of music videos and MTV. However, I still like a lot of the music out there, especially the less popular music.
Live music still is the best if the soundman is good. I used to see a lot of music live at the Caravan of Dreams, but they closed it down. In my area there are hardly any venues for live music that are small with a decent sound system left.