What are you 'TRULY' Looking for in Loudspeaker...

Natural tone
100% coherence from highs to lows -> solid timing-> musicality
Weight AND speed -> lifelike timbre, presence, immediacy
Pinpoint imaging -> instrument separation

Planars lack in imaging, single driver speakers lack in body/weight and tone on both extremes, 2 way dynamic speakers either in the bass weight and / or midrange transients. Most speakers have problems with coherence in mass and speed, especially ín the bass region.

Only the 2 way transmissionline speakers (good coherent bass speed but without weight) or 3 way speakers with small woofersize around 5" (-> speed, accurate timing, midrange driver got to have the same size) worked for me so far.

Not to get crazy here, I assume that you mean listening criteria not physical.
#1 Tonal Balance
#2 Soundstage (do they disappear)
#3 Imaging (can I point to everything on stage)
Then I assume mated with the right electronics that have synergy with these speakers that the combination sounds like music.
There are a few more factors but these 3, I am somewhat fanatic about.

"What are you 'TRULY' Looking for in Loudspeaker...
and system?"

Gotta sound "right" and be able to afford it.

"Have you really studied the options and do you really understand what they can possibly give you in return?"

Yes and generally yes.

I can't help thinking this is a very oddly put question. Dale, if you asked simply what we are looking for in a speaker, do you think we would all lie about it? Why in the world would it ever occur to us do that? Or why would it occur to you to think that we would?

To give you a very, very honest answer, I look for a believable representation of the natural timbres of unamplified instruments as well as a reasonable facsimile of those instruments playing in a concert-hall space. I swear to God, I am. And I mean that from the bottom of my heart.

Very sincerely,
-Bob

"To give you a very, very honest answer, I look for a believable representation of the natural timbres of unamplified instruments as well as a reasonable facsimile of those instruments playing in a concert-hall space. I swear to God, I am. And I mean that from the bottom of my heart."

This sounds quite reasonable to me also. I would only add that I always want to be connected to the performance, most important.