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.
It was the one with the highest lvl.
I had one real wolf lvl 1 a shadow lvl 80 and a ganesha lvl 70.
To be shure I checked all three towers.
None got the pack bonus.
Thanks for reporting!
I filed a bug for it, I will try to reproduce and create a fix during this sprint.