Cloning hard drive with skype install?

Hi all, I can't see a clear place to ask this question so I'll post here. I am getting ready to roll out skype to a couple dozen computers and I will be cloning all of them from a single master image. I know that some software doesn't like it when you do this, and one of the people I am working with on the project suggested I look into pottential problems with skype.
So,are there any problems(software licence-wise or technical) that would prevent me from installing skype to the imagemaster, preforming a sysprep operation, and cloneing the drive 20+ times? If so, I can certainly install skype after the image is done, but if you've done things like this you'll know its best to avoid as many little "after cloning" changes as possible.
Thanks!

Is disk utility really no good? Does that explain it?!
In that case I'd better get ccc or superduper later but right now i only have 500MB space left on my mac so I can't add anything more. I've had a look at what I've achieved so far and the copying stopped in the middle of an old xerox printer plugin in the library after 1 hour of slow but good work. I finished copying the library by drag and drop and it all looks the same as the original. That leaves previous systems, systems and users. Can I just keep going by dragging and dropping?
Right now my problem is that I tried to copy previous systems and after nearly 2 hours it is still 'preparing to copy' and i can't stop it, it doesn't respond.

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