How to meaningfully audition speakers??

I dont think it's as simple as the old digital vs analogue argument. I've heard enough good sound and bad with both formats. I blame the ability (or lack )of the recording engineer. There are excellent sounding digital jazz recordings, so it obviously can be done.there are some vinyl pop and rock efforts that are awful.

Frogman, I didn't intend to limit the obvious possibility of type casting as it's usually based on a kind of truth: I just wanted to avoid generalities though they most certainly apply (and I didn't want to be the first to say it, not having the expertise).

What you say about the industry, in general, speaks volumes. Solutions in search of a problem that never really existed. Technologies used that overstep their intentions.

When you speak of SOPHISTICATION IN ITS SIMPLICITY AND ACCESSIBILITY, I'm reminded of MA Recordings, Mapleshade, ECM and others that always seem to get it right. They can capture the moment, the intent, flow and emotion and bring it to your living room.

All the best,
Nonoise

Frogmam,
Thanks for your very insightful perspective. You mention the engineers having less reliance on actual listening to the musicians play and are instead in the booth. This one factor explains plenty! This approach would seem to lead to fixing a product that requires no (or minimal) fixing or tampering. There's probably an overwhelming desire to utilize available technology and gadgets just simply because you can rather than true need.
I also agree with vyour point concerning microphones, it appears mutimicing is over relied upon and often does more harm than good. The simpler microphone use of the 1950s stereo era have clearly stood the test of time.
Charles,

It has nothing to do with analog vs. digital, specific mics, multi miking or even the experience of the engineers. There really is no simple answer and therefore no simple fix.

Basically it has to do with differing aesthetics. How a classical or jazz recording is supposed to sound is very clearly defined. For jazz it should sound like "Kind of Blue", one of RVG's Blue Notes, or maybe like an ECM recording. Because jazz has such a well defined sound there are a whole list of things you don't do when recording/mixing a jazz album. For instance you wouldn't use a non-lin reverb on the drums. No compressor on the bass. No vocoder effects on the vocalist. Don't shift the sax from the left to right channel during his solo. There are just things that you won't think of doing on a jazz recording. There are no such rules or prohibitions in pop/rock recordings. Because of this the sound of pop/rock recordings is very variable. For some engineers it's a case of too much freedom and the sound quality can suffer.

Ultimately, talented musicians working with talented engineers are more likely to make good sounding good music than other combinations.

Note that most musicians are surprisingly clueless about sound mixing regardless of their talent as musicians. The good news is there are zillions of great sounding recordings to enjoy, and some are new...Also you really can't "train" engineers to do anything but know what knobs to turn as recording esthetic is more in the "talent" or "art" genes and that quality remains mysterious. Example: A very well regarded female singer/songwriter came to play at a concert I was mixing (I designed the system and had been mixing this monthly concert series for years), and brought along a young dude she trusted to mix for her (a few higher profile artists liked to do this, and I usually don't mind at all since they're usually fine)...this guy was amazingly incompetent in every way, although he claimed to be a professional studio engineer. NO idea how to use trim pots for mic balance, no sense of the room sound...man...and this resulted in our first show EVER where people thought the sound kinda sucked. The end.