I use a "tiered" approach when evaluating differences, starting with Redbook/cd quality recordings, moving to high res digital masters and finish off with "direct from tape transfers".
In Redbook/cd recordings I mainly focus on PRAT, dynamics, staging and reasonable density. As these are usually not as sophisticated and more "mechanical" sounding then higher resolution files I evaluate things like air, flow, naturalness, tonal beauty, shading, differentiation and saturation in later stages. Nonetheless this is an important stage as a very significant part of our music collection is only available in this format.
Bob James, Urban Flamingo, Track #6 Fresh Start has to be engaging and bursting with attack, it is very easy to pickup differences on this track, if rendered correctly it causes a feet tapping experience for the full 7 minutes of the track. If I find myself hitting the stop button at 2 or 3 minutes in something is wrong. Correct piano positioning and size is something to focus on in this track.
Harry Connick jr, Chanson du vieux carre, Track #8 Luscious, a bit rawer, needs to "pop" with proper bite, attack, jump factor and dynamics, looking for a degree of authenticity as far as the format allows and focus on "fun" and entertainment factor.
Sam Cooke, Night Beat, Track #2, Lost and lookin', suffers from a slight "digital edge" but can sound beautiful with decent differentiation and good tonal shading.
Ennio Morricone, Super Gold Edition, I do tend to go through a few spaghetti western well knowns, recording quality is not great, but it has not been "mastered to death" either. Can have surprisingly good definition and spatial rendering with some fun sound effects. Disc #2, Track #13, L'arena for example.
Hans Zimmer, Live in Prague. I'm a big Hans Zimmer (and movie) fan. I always try to find to match listening to the movie soundtracks to the full movie atmosphere experience. I used to include a wide range of his studio recordings in my evaluation cycle but switched to this live recording when it was released a few years ago. The tracks have a higher degree of authenticity and are more lively and thrilling then the studio versions. I happen to personally know the sound engineer designing and operating the live sound reinforcement systems. He lives about a 15 minute drive from our workshop in Hengelo and I have had the pleasure of having him over here listening to his efforts on our system. Fun fact, his home system consists of stacked Quad ESL57's, augmented with full size Pro AMT tweeters, driven by Quad II tube amplifiers. All restored/reworked to suit his personal preferences. His PA system designs all use ribbon tweeters, needless to say the Alsyvox Botticellis we were using at that time got his thumbs up. Back to listening, this contains some large orchestral pieces which build up to some very and busy scenes. There are over 200 microphones used in this recording to illustrate the complexity of this recording. What I look for is if the system can maintain a full overview as the orchestra builds and builds and if it can "climax" properly. This is a challenging task for every component in the system. There is a 24/48 version on Qobuz, and a 24/48 MQA version on Tidal, but I prefer the 16/44.1, the "higher res" versions add some detail which sounds artificial to me. I do at the very least play Disc #1, Track #6, Pirates of the Caribbean and Disc #2, Track #7 Inception, but often find myself listening to all tracks.
@Mike Lavigne , these are the tracks I played when visiting you which you referred to as "torture tracks".
Moving on to high res recordings:
A more recent addition replacing a few others is this 2xHD Fusion album, transferred from master tape with high-end equipment. Details on the transfer process can be found online. This results in quite a different sound quality from digital (re)mastered pieces. I really like the presence, 3 dimensionality and feel of Track #6, Route 66 but all tracks are worth a listen and I usually play a few of these. This is all considerably more real and life like then the previous listed material.
The Bill Evans Trio, At Shelly Manne hole, a 1963 recording transferred directly from tape by a process called "PureDSD", the idea here is that as DSD cannot be edited without being converted to PCM and subsequently back to DSD, you have some guarantee you are listening to the original analogue master. You can buy this from
https://www.highdeftapetransfers.com/ in DSD256. This has all the noise, hiss, flutter and imperfections you'd expect from something not cleaned up to today's standards but in return you get something very pure with all original harmonics and shadings intact. This is where I start focussing on air, flow, naturalness, tonal beauty, shading, differentiation and saturation as it has this in spades. Usually simply start at Track #1 and "let her go".
Duke Ellington, Indigos, a 1957 recording, transferred in DSD128 "PureDSD", really along the lines of the previous recording, start at Track#1 and often end up playing the whole album.
Sarah Vaughan, After Hours, another "PureDSD" in DSD256, recorded in 1961. A bit "rough" but Sarah's voice is all there with all it's intonations and shadings. All these HDTT transfers do a good job at transporting you 60-70 years back in time with the recording sounding as you'd expect it to having sounded back then. Also simply start at Track #1.
I'm going to cut it short here noticing the time. Another transfer from HDTT in 24/352.8, recorded in 1963, not PureDSD but still good with a good leading edge to the Sax, very alive, raw and a good dose of naturalness.