To me it's simple. When I sit down and pop in a CD with a nice glass of whisky, do I forget where I am/lose myself in the music? If so, I'm done. You can always tweak a little here and there with room treatments and isolation but nothing in the system itself (speakers, pre, CDP, amp and cables) should be changed at that point and going forward.
imo, upgrading when you've reached the aforementioned point is simply an attempt to compensate for needs not satisfied in other parts of your life (for me, I tend to go shopping for tech stuff when I feel bad and I've learned to limit that a lot as it got me into more trouble).
Perfection on earth doesn't exist, happiness is all we can really hope for. Searching for perfection is a fruitless pursuit in audio or elsewhere.
Caveat: I don't consider myself an audiophile, just someone who loves of music.
imo, upgrading when you've reached the aforementioned point is simply an attempt to compensate for needs not satisfied in other parts of your life (for me, I tend to go shopping for tech stuff when I feel bad and I've learned to limit that a lot as it got me into more trouble).
Perfection on earth doesn't exist, happiness is all we can really hope for. Searching for perfection is a fruitless pursuit in audio or elsewhere.
Caveat: I don't consider myself an audiophile, just someone who loves of music.