How good is good enough?

OP,

You bring up a really important issue. Once you upgrade, then you play music.

If you have a detail scraping system… you end up hearing the worst possible rendition of any recording… only the very best recordings sound great. If your system is musically oriented then most recordings sound great and the ones that sound great on a hyper detailed system sound extraordinary.
 

You have to be very carefully on the criteria you use to evaluate potential components. If it is the most details you can hear, then it is likely to end up, bringing out the shortcomings of every album and not it’s strengths.

@rvpiano It’s very easy to go down the rabbit hole if you listen for defects instead of listening to the music.

Agree with this statement by rvpiano. Also, I'm observing once again why its important to give a new system or new components time to settle in.  Its not always  about 'just getting use to it". There can be change that occurs, given the chance. 

Patience helps from jumping out of one rabbit hole to another rabbit hole. 

Isn't this a question every audio crazy has to answer for himself?

Yes!