My 7 year old self most enjoyed music in '63, listening to "Love Me Do" on WABC under the blankets on a transistor radio on a winter night...
My 16 year old self most enjoyed it, on a rooftop in San Miguel de Allende, Mexico, under the stars, listening to Otis Redding on a portable cassette player, drinking from wine from the bottle...
My 17 year old self most enjoyed it in Southern CA, 1973, staying up all night in a high school friend's attic bedroom, listening to Live At Leeds, Allmans at Fillmore, Derek and the Dominos...
My 20 year old self most enjoyed it living in Santa Barbara in '76, when I could wander a few blocks from my apartment to spontaneously catch artists like Jean Luc Ponty at the nearby Arlington Theater. Ticket prices were very low and that town was a live music paradise.
I could go on and on... I don't think the intensity of my love of music has changed, although it's certainly evolved to meet changes in me, as have my tastes. When I was a confused adolescent, music met different needs than it did when I was 30, 40, 50 or now, as a retired, 65 year old.
Being able to afford a decent system is a relatively recent phenomenon for me, so my memories of life-long listening enjoyment have little or nothing to do with gear... and I wouldn't have it any other way. I enjoy good sound but would never want my enjoyment of music to be dependent upon gear!