Great thread.
Seems like you guys have this all covered.
The list of possible roles seems VERY complete, particularly with the addition of the judge and soothsayer...with kinda goes along with one of my only additional suggestions to include Astrologer.
I also was thinking, possibly, as a "balancing" role to the hunter to have a "Handler" or "Gameskeeper"...someone who is specifically attuned with the animals of the region.
Just an idea.
You've got the wiccan thing going, which I also incorporate into the druidic order in my world.
I also have incorporated the "elementalist" type specialization, but in the druidic order, they're a "balanced-all elements (or the cardinal 4)" specialist, not specifically a "fire-oriented druid" or an "earth-oriented druid." (as cool as I thought Avatar-the animated one, not the blue people
My only OTHER possible suggestion you MAY want to incorporate, which would work with your wiccan symbology and could easily be incorporated into the seasonal break up, would be a sun and moon split. A sect of the organization that is sun-based and one moon-based. They would still be part of the same order, of course, just certain druids who were attuned/assigned to the Moon-sect (and those things more associated thusly) and those assigned to the Sun-sect.
But that's a completely optional organizational thing for you to decide with your order. I don't do it in mine, but was a thematic thing I hadn't seen anyone suggest yet....So there it is.
Good luck and happy druiding.
--Steel Dragons