I like the idea of a bear with improved Shillelagh using a 3[w] quarterstaff, picking up a couple of levels of rogue for dex to damage (if useful) and 15% extra attack speed with a staff. Not sure if it would work in practice, but I like the idea.
However,
(A) most of the newer staffs are not wood. Especially those with improved crit profiles
(B) Unsure whether the Rogue's attack speed will work in animal form.
(C) Imp Shillelagh doesn't currently do anything. (see https://www.ddo.com/forums/showthrea...=1#post6078126)
(D) It's unclear to me whether "doing an extra 1[w] damage" means the [w] goes from [1d6] to [3d6] which would make a +2[w] Great Cleave do 9d6, or whether it stays at [w]=[1d6] and the Shillelagh damage goes on the end of the calculation, meaning a +2[w] Great Cleave would be doing 3d6+2d6. Also unsure how it goes with the crit multipliers. If it actually increases the definition of the [w] then a [2d4] staff would be doing 18d4 per target on a great cleave, which would be nice. If it just tacks another 4d4 damage on the end of whatever [w] calculation is done, then it's only as impactful as a poison. If it increases the multiplier from, say 4[w] to 6[w] then it's somewhere in between I guess.
(E) It'd probably be more useful as a wolf, but I like the idea of a bear anyway. Flavoursome. And more cleaves.
It'd be very nice if we could get a higher level version of something like the Staff of Inner Sight, http://ddowiki.com/page/Item:Staff_of_Inner_Sight which allows for WIS, CHA or INT to attack and damage, does [w]=[2d4] damage, and is wooden so it's affected by Shillelagh. But we don't have it, so this whole idea is probably not worth even fleshing out.