I'm surprised there are not a lot of responses to this perfectly reasonable posting. As it happens, there are "annotated playlists" (and CDs) that are specifically designed to demonstrate various audiophile virtues. Consider, for example, Chesky's "The Ultimate Demonstration Disc: Chesky Records' Guide to Critical Listening." This CD contains 30 tracks, half of which are voice announcements that tell you what each track demonstrates and what to listen for. A sampling: "Depth"; "Atmosphere"; "Midrange Purity"; "Transparency"; "Rhythm & Pace"; "Holographic Imaging." And so on. The voice announcements are brief (less than 30 seconds), and the musical examples are all well-chosen to illustrate what the voice announcements describe.
Another Chesky Records disc ("Jazz Sampler and Audiophile Test Compact Disc") contains, besides sonically dramatic musical tracks, the famous LEDR imaging tests that are difficult to find elsewhere. These sounds, created by computers at Northwestern University in a sound lab (Chesky describes them as "the world's first objective stereo imaging test"), demonstrate stereo effects left-to-right and also above and below.
Then there are various favorite familiar tracks anyone has easy access to that are recommended by particular individuals to demonstrate particular system abilities. Among my favorite are three tracks used by the CEO of Sonus Faber to show off his speakers: "What a Wonderful World" by Eva Cassidy; "You Want it Darker" by Leonard Cohen; "Diamonds on the Souls of Her Shoes" by Paul Simon.
Finally, some of us have put together our own "mix tapes" (as they used to be called) of favorite demonstration tracks. Musical taste (i.e., "subjectivity") comes into play for all of these options, of course, but at the same time, when the primary criterion is audio quality—or, in fact, some particular audio quality—then there is some "objectivity" to the selections.