Britishbane, What do I look/listen for while auditioning
Wow. Thats a good question. Do you listen to live acoustic music? If so, that would give you a great reference, because dont we all want our music at home to sound like it is the real thing? I would go for the gestalt, the whole experience of if the music involves and moves you, not audiophile little details of this or that. You need experience, lots and lots of listening to different systems to determine what you like and what you dont favor about reproduced sound. It is a matter of no one else's but your interpretation, and whether you prefer it. I cant tell you what that might be (and neither can anyone else). Thats the good and difficult part of all this and it will change with experience.
As many have said before me, at this point you have a pretty solid source. Rarely would I suggest it yet, in this case it sounds like upgrading the preamp/amp to get the most out of your source might be the best bang for the buck.
Remember system synergy is very important and highly overlooked.
Inevitably, the speaker/power amp synergy is a very particular thing. The marriage, if you will, must be harmonious and I wouldn't purchase speakers and/or power amps without a great deal of thought for the future and auditioning them together to make sure you get the magic.
That said, your system is only as good as the weakest link and although I would normally advise toward a greater (analogue) source because, it is just that, the beginning of the chain and could be vastly superior to the rest of your system and yet enable you to have a reference and grow with all other down stream components for years and through many iterations.
Quite frankly I think you're correct and smarter than your years about the speaker/room scenario at this time.
With a reasonable investment in a used preamp, say a Modwright SWL 9.0 Se or Audible illusions Modulus 3A, you would resolve huge amounts of detail, dynamics and finesse and still have some cash to bank toward a power amp for your B&Ws or for a different pairing of speaker/ power amp to take you to the next level, which ever you prefer. I would guess the question here is how much do you like the speakers you have? But again, without a higher resolution preamp and a proper match in power amps, how would you know?
Anyway, both the source you have and a finer preamp will help you figure out were to go next. This pursuit for high fidelity is not easy, as you may have gathered, but I for one can assure you it will be very satisfying with a little hard work.
Happy Listening!