Mark W. Johnson
Does melee combat continue until all of one side's units are eliminated? If so, does the attacker continue to roll (re-calculating the odds each time)? Or does the defender 'counter-attack' with the next roll?
There is only one "round" of melee combat per melee sub-phase. Surviving units are free to move/attack the following turn regardless of whether or not they begin the turn co-located with enemy units.
If the Outlaws loot Sir Guys keep before he is activated, is that considered an attack? I would think so, but I cannot find this explicitly mentioned in the rules...
If the Outlaws enter and exit the keep through the secret passage and thus do not move into the castle space containing the unactivated Sir Guy, they would be free to loot the keep. If the Outlaws instead move into the castle space, I play it they would have to cease movement and attack Sir Guy before entering the keep.
I believe this is the intent of the rules since it is specified that unrecruited Outlaw units cannot be attacked or molested in any way, but Sir Guy may be attacked while he is not active. Between that and the 6.2 rule that states "A unit or Leader must stop on entering a box containing enemy unit(s) or Leader(s)," I don't think it is possible to simply pass through Gisbourne Castle and loot the keep while basically ignoring the unactivated Sheriff units present.