You can go home again

No I think the more equipment you can hear the more you will understand what you like. Unfortunately this leaves a bank account that slowly vanishes. 

Do we presently chase a sound baked in our brain from our initial experience with audio?

No. But "we" do jump to unwarranted conclusions, don't "we"?

Yes. I think that is frequently true. For me I had a memory from rock concerts and early “good” systems I heard. It took me decades to slowly realize that the treble I was chasing was actually distorted high frequency hash (one characteristic). Over time as my systems got better they kept pealing off the distortion and the sizzle that I remembered went away… it was disconcerting. But I realized what I was hearing was much better and more accurate to the instruments.


Over time I made a concerted effort to listen to real unamplified instruments and adjust my expectations. All music types on my system improved dramatically. I struggled with rock… since it is always electronically reproduced and unless you are in the mastering room you can’t really have an empirical ruler. Ultimately my conclusion was that if I only listened to rock and wanted to get that sound right I would have to get a set of JBL speakers. Of course that would have implications for all othe music types.