Changing the transparency of a head decal doesn’t work.
I’ve tried and there are no problems for unions, custom meshes, and every type of SpecialMesh except Head meshes and Sphere meshes; they have the same problem.
It also works on other bodyparts besides the head.
This is because the face texture is composited as part of the overall humanoid texture and is not drawn like a regular decal. I looked into making the transparency property work for faces briefly a few weeks ago and didn’t see an obvious way to do it. I’m sure it would be possible, just need to spend a bit of time on it. I will file a bug and see if I can fix this at some point.
It can work, it just happens not to. You know where to find me if you want to fix this 
Submitted a fix for this, should be released in around two weeks.
This is fixed now.
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