Years ago when first getting interested in hifi, I heard certain ssytems from time to time that let me know for sure there were things in the music to hear that I was not hearing because my players were not that good.
Then for several years after some improvements I was satisfied, but not pre-occupied with having "it-all". So I got by for many years that way.
Then about 2008 or so, I realized my old Maggies could no longer cut it for me in the different room I needed them in, and decided to fix it an not stop until completely satisfied I am doing things "right" and not feeling shorted in any way.
So after many gradual upgrades and thousands of dollars later, that is where I have been for most of the last few years. Don't regret any of it. Now I just wonder how much must I really invest down the road to stay satisfied. Like most things, the answer is still it depends but I become better educated about what does and does not work all the time along the journey.