I cant seem to Cut a hole in Any objects with the Difference operation while using the Boolean Modifier, All it does make Objects Disappear or Instead give me an Error(Unable to perform Boolean Operation)
It appears that your mesh with the Boolean modifier is a 2-dimensional plane, this will cause some issues with your Boolean operations. I noticed some very unusual behavior when trying to perform a Boolean operation on a 2-dimensional mesh (final result, difference mesh has been deleted):
However if I extruded the plane a small amount, the result was completely normal:
I think you will have to add some thickness to your mesh before using the Boolean modifier if you want to achieve expected results.
Also see this answer to a very similar question.