Readin this and a few things came to mind.
Get an Act 2 Might Merc. Equip him with the 21 thorns bramble, give yourself an enigma for an extra +2 skills. Slap a pride on him and you get more damage, and find a way to keep him in town, I.E. stand as far away from the entrance as possible. Or if your playing in a game with the entrances to the left, the top and the bottom, you can tele him with your enigma behind the wall and your bear will still get the auras.
Prebuff with Hoto and use Beast on switch.
If you get to a higher level you could probably start to max out HoW.
Bear + Synergies + Fana + Concentration(pride) + Might + HoW/Oak + Thorns = One mean bear.
Any by the way, as it comes to NK'ing and making people cry, couldn't you just prison them as they run out, cast your bear on top of them and laugh?
Great guide, I might just make one.