Back to the OP: one thing to remember with DMB is the vast age spread represented by the individual members. At the beginning ('94) Stefan was 16 while Carter (the oldest) was TWICE that age, at 32 years old. Dave was the second youngest at the time, at 25 years old, still 9 years older than a kid barely old enough to drive.
Let's also remember that in 93/94 Carter was just coming out of teaching in public schools, where he could have been teaching kids who were Stefan's age!!! At the same time Stefan is coming out of school, . . . as a student!!
So, it would be only natural for Stefan to sort of yield himself to the rest of the band, particularly Carter, who was twice Stefan's age and who has a very dominant personality. (Check out the youtube of Carter being angry at a concert if you want evidence of his dominance.) Stefan himself speaks of Leroi and Carter in almost fatherly terms, you know?
So, that age dynamic is definitely going to play itself into the formula.
If you go back and listen to the earliest live stuff available, it really is quite amazing what Stefan was doing at such a young age, surrounded by so many excellent musicians who were that much older than him; and he was doing it in an environment where he was always the kid in the room. Hats off to Stefan!
For the last 3 years I have been working my way through the DMB/Lessard catalog. I think his playing is the perfect blend of jazz/blues/rock styles to emulate if one wants to get better, faster.