I tested the Wolfskin cloak. It gives only the fixed bonus, but not the pack bonus.
If a cloak makes a tower a pack member, it should also work with only two towers each wearing a WSC.
If you have two towers wearing as WSC no tower gets the pack bonus.
If you add a real wolf still no tower gets the pack bonus.
What should happen if one tower wears two WSC ? Double pack bonus? Is it counted twice for the pack bonus?
Is it a pack on its own with only two members or three or four or even more for Mr. Iron?
How about a lvl 80 Mr Iron with 5 WSC ? Is it a pack with 5 lvl 80 wolfs?
This sounds like a bug to me! Just to make sure I have to ask this: Was the tower you gave the cloak to, the 'Wolf' with the highest level on the map? Because only that guy gets the pack bonus.
As for your second qustion, a tower can only count as one Wolf, no matter how many cloaks this tower is wearing.