Picking Speakers 20k-30k

Definitely take your time. Speakers in the range you are looking at are really good and very different. You want to hear them… holding off until a speaker connects with you. @grislybutter had a pretty good list of must hear. You also need to take into account what equipment the folks demonstrating the speakers are using. I would take your time, make it a fun exploration. 
 

Do all this before upgrading any of your electronics. If you want the very best sounding system it is best to choose your speakers… the component that will most influence the sound and then buy the electronics to best support the speakers and the sound quality you want. 
 

just going through this process is likely to change the direction of your search. This is why auditioning (then reading professional reviews), can slowly lead you to a great synergistic system. Unless each purchase is carefully chosen with the whole system in mind you can end up with a very expensive and unsatisfyingly sounding system.

OP… “But it’s a super-resolving system and lesser recordings have their warts on full display”.

This is one of the major themes of high end audio. I struggled with this off and on for thirty years… of my fifty year history in high end audio. This exact issue. Say on one end (1) you have a warm emotional system with poor detail and on the other end you have an ear bleeding - scrape every detail from recordings system. I’m guessing yours is 7 or 8.

The biggest determinant is typically the speakers… but in no way the only component… every component contributes. I have nudged this relationship at every stage of upgrading my system. The good news is you can have both.

Having both requires work and money certainly helps. In general everything gets better at larger levels of investment. However some folks love systems that sound like 1 or 2 and some love systems at the opposite end of the spectrum. While lots of money makes equipment quieter, less harsh and more musical… there is still its intended audience.

I was into highly revealing planar speakers and high quality solid state equipment which frequently put me too far into the detailed 8 - 9 range.. where all but the best recordings did not sound great. Ultimately i changed directions and I purchased my first set of Sonus Faber speakers which I have been upgrading for the last fifteen years… then I have added all tube electronics. All very carefully curated to move me to say 4 and then with better and better components maintaining that balance. Often you can look at this continuum to be musicality versus detail. My system is detailed and very musical. The product of decades of learning and investment to nail this perfectly for me. All but the very worst recording sound great… detailed, but musical and forgiven.

So, you bring up a really central question when building a system. My only recommendation is to go listen to some Sonus Faber speakers (preferably powered by good tube electronics)…. Well beyond your budget is fine. You want to find your target. If that is it… then scale down the speakers to ones you can afford, and over time support them with electronics that nail the balance you want.