Alex, First, nice thoughtful post.
My POV is a bit more simplistic perhaps, but I believe most folks are anchored to music they found appealing during their youth and unless they developed a serious interest in a particular idiom they, at least subconsciously, resist the progression this music takes . Some resist and reject this evolution and dismiss it. Some enjoy and encourage this progression, more food for their brain I think.
I came to jazz when I was an adult so I had no fixed opinion about the value of music from the introduction of recorded jazz from any particular period. Blessed, perhaps with this ignorance, I was free to explore/like/reject music from all of the various periods and styles of jazz.
What I found, and it was an experience I had in dealing with the evolution of classical music from the 'classical' period thru the 'modern' period was that each new period required some attention and, more importantly perhaps, just passive acclamation, to the form and the sounds.
I was in my Beethoven period and dating a woman musician employed by a symphony orchestra. She was helping me with my Beethoven experience and casually mentioned that she most enjoyed playing Shostakovitch's music. I listened once and was baffled by all the noise. I didn't listen again for perhaps 10 years. Now I've blown through his music (an a lot of other from his period) and have learned to accept and or reject his compositions based on nothing more or less than my appreciation.
I think what has saved me from anchoring myself to Beethoven's period was nothing more or less than a native curiosity. I feel fortunate in my approach to Jazz. I feel no more reluctance in listening to the music of , for example, Ron Carter, Brad Mehldau, Charlie Haden, Roy Hargrove or Joshua Redman than I would to the music of Henderson, Jones, Getz, Evans, Benny Carter, Peterson, (and all of the famous players from the 50's, 60's and 70's).
I think there is nothing wrong with 'personal feeling and experiences' controlling your personal enjoyment of the music but, like you, I fail to find it a credible basis for argument, or any valuation for that matter.
One of the things that I most enjoy about both Frogman and Learsfool is their continuing interest in the music itself without a chronological anchor. A trait I think most musicians share.
I apologize in advance for this wordy, self absorbed perhaps, explanation of my views.
