how do you gauge and judge "timing"?

It could mean that the speaker crossovers and components step response are set such that the sound of tweeter arrives first and as it decays, at the bottom (top for inverted polarity), the wave blends with the beginning of the midrange driver’s signal arriving.  This then decays and at the bottom (top for inverted polarity), the wave blends with the beginning of the bass driver’s signal.  This is considered as optimal crossover topology.

https://en.wikipedia.org/wiki/Step_response

https://www.audiosciencereview.com/forum/index.php?threads/step-response-does-it-really-matter.1999/

Huh? Difficult to identify? Norah Jones and Diana Krall ain't PRATty...Listen to artists ortracks that are PRATty dude.

For example, here's something PRATtier than boring Diana, Norah and that boring side of the moon, I suppose ...

https://music.youtube.com/watch?v=PG9DEaE1HXI&si=cFk-Kh4VnYueWbxD

It shall also let you know if your gear is kinda PRATty or kinda CRAPpy perhaps.

Just as a comment on PRaT. It is probably one of the most important characteristics there is in music. It is what involves you emotionally and makes you tap your foot an sway. It is also one of the most difficult to sense and identify.

Oh and dont listen at 50 db and become all non-PRATty and fall asleep.., listen at 90 db.

It's how the notes "land." There, that settles it.