This is happening both on our windows and mac machines.
In focusing just on our Mac side. We're on 10.8.4 on a pretty large range of hardware, but I've been focusing testing solely on the 1 TB Fusion iMacs.
We are making a master image. I would deploy it modularly using something like Munki, but we have a lot of After Effects plugins, and camera plugins that need to be configured.
Our issue is that it works before pulling our image to our DeployStudio repo but when deployed I'd say now we're seeing about an 80% fail rate. When users try to launch any adobe products, they'll be prompted to sign in before our "7 day" trial expires. I've read on one of my mailing lists that an Adobe Engineer said Creative Cloud doesn't support being deployed on a master image.. but this is in direct opposition to what our Rep told us when we were purchasing..
I've also noticed that in order for InCopy and Dreamweaver to launch without errors they require opening up some permissions on their application folder, otherwise it fails to detect some plugins.