Kevin, that's a cool attitude to have, recognizing that even if something isn't your cup of tea, that doesn't diminish it's potential significance as an influence to you.
While Phil is probably my favorite bass player, I have never spent much time trying to exactly learn his parts. With the vast library of recorded material available, how could I? The stuff he may have played on a particular song on a particular night was influenced directly by what the other players were doing at that moment, and might not fit with whatever group I am playing with when I play those songs. I am influenced by his approach, however, and when appropriate, try to apply the blend of support and counterpoint that he usually does so well. (Of course this is oversimplifying his style, but if you listen to him then you don't need my personal take on his playing.)
The Dead (and other jam bands, as well as jazz) are interesting in that it's more like watching your favorite baseball team than listening to the average band. While there are basic structures and signature phrases (9 innings, offense and defense, fastballs, curveballs, etc.), there are major portions of the music that are different each time it is played. Sometimes it's good, sometimes it isn't. People don't stop watching just because their team doesn't go undefeated, however, and the home runs are that much sweeter when they happen precisely because they don't happen all the time.
The analogy fails, however, when it comes to the idea of best. While we can say that so-and-so was the best pitcher of all time based on of our reliance on fixed performance criteria, music is largely a subjective art. Certainly, there are degrees of technical competence, but is it on technique alone that we base our conception of good music? I have had the priviledge of seeing Oteil Burbridge both in a 300 person club with Col. Bruce and the ARU in the early '90's, where I was probably 10 feet from him and getting my mind blown wide open by his technical prowess, and then seeing him in the late '90's from the fourth row at a 1000 seat theater in Macon, GA, when the Alman Brothers played a memorial show for one of their road crew, Joe Dan Petty (our wives worked together), who died in a plane crash. Instead of his 6-string Modulus, Oteil was playing a Jazz bass, and while he didn't wow me with flash, there was a purity and reverence in his and the rest of the band's playing that literally brought me to sobs of both sorrow and joy. While he may have been technically better in the first example, the second was by far my favorite, and a much more gratifying experience, both musically and spiritually.
Kevin, just to make sure you know, I am not disagreeing with anything you wrote, just adding my opinion. This is a topic that I have debated many times with friends, but had never bothered to write down before; now seemed like a good time.
Have a safe and peaceful weekend,
Charles