I have ALL the Dick's Pick's and almost every Dead CD. The BEAR recording always seem to have that little something extra that just sounds "cooler"! Although I LOVE the music, some of the Dick's Pick's sound really "weird" (that's a technical term)---> the sound may be crisp and clear but there is no depth at all.
Check out Katie Mae on Bear's Coice (HDCD version); could be my favorite. Pigpen's voice sends a friggin shiver down my spine everytime I hear it. My wife is like, "why do you always listen to that same song"? Turn it up really loud and listen to the sounds you hear in the corners of your soundstage.
The question specifically asked for Dead recording. However, for sound quality the Grateful Dawg recordings are simply THE best "Dead" recordings out there hands down (for sound)!
I have not yet heard that Filmore recording, but I may go buy it right now.