Too PRO-CUSTOMER support

It's huge tin of worms though, and you should be very wary.
As soon as yout start getting into things like configuring the network, firrewalls, datbase servers etc, impacting back up policy, performance, you are on your way to a world of hurt.
Just something as simple as needing to get fully patched as a dependency, breaking something that was working, where do you go from there?
Once you start burgering about on their system, near anything goes wrong, whether it's anything to do with what you've done or not, you are on very thin ice.

We don't allow company software on non company computers. We don't allow personal computers on company property, or to VPN into our network.

We do have an arrangement with MS to allow our employees to buy MS office license cheaply, but they are soley responsible for installation.

Its a big can of worms, even moreso now with wireless network etc.

James

If those headaches aren't enough to convince the CIO that there's trouble ahead, then I'd be nervous.

If they need the software that badly, get it hosted and give them access through the web.