Consistency
The biggest problem I see is keeping the workforce on an even keel. Small business' already have the issue of not wanting to limit the workforce from supporting themselves to avoid having to pay IT people to do routine and mundane tasks. But now instead of having someone running a .0.X different version of Entourage or Outlook, it becomes very easy (not that it was really hard before) to have people running significantly different operating systems. I am a huge fan of making managers manage their people's behavior rather than forcing the IT folks to be babysitters, but this may be the time to start locking down the boxes. Or at very least start providing much more specific information to the end users about they can and cannot do.
