Reika – When removing Roots and dealing 2 DMG to myself as the Voidwatcher, does Masochist trigger?
Yes it triggers Masochist giving the Voidwatcher a Bonus Die!
Titan’s Juggernaut also shields the DMG to himself, but using Challenge to try to reduce the DMG to allies will not work because the self damage is not Boss DMG.
Dragoon’s Airborn does not reduce the DMG from removing roots, because it is not Boss DMG.