You write very well! Also you have put things in perspective - with which there’s always a risk of losing because hobbies and passions become so consuming.
Can you help understand why you say “aesthetic sensibilities evolve from generation to generation and take varying shapes in terms of associated equipment”? I’d think it’s ‘values’ that evolve/change from generation to generation and also within the same generation as we age. For example, a teenager is likely to value mobility and freedom while mid-ager might value leisure and relaxation. And these are likely to influence their choice of equipment and listening environment. But when it comes to aesthetic sensibilities (that influence our choice of music and musicians), I’ve found it to be more individual specific than generation (era) or age specific. I find many youngsters with heightened (aesthetic) sensibilities as well as many in their forties and fifties with blunted sensibilities.
One could argue against this pointing to how aficionados in their seventies today would listen to Shamshad Begum, those in their fifties to Lata Mangeshkar, and those in their twenties to Shreya Ghoshal. But I don’t see it as a result of different aesthetic sensibilities - all three choices reflect fine /classic sensibility. The difference is only because of the attendant factors that are era specific - and those include (but not limited to) lyrical content, musical arrangements, recording techniques etc.
Thanks for triggering this reflection.