re: 5 Things CFOs Hate About IT
If CFOs really follow the thinking that you've outlined in point #2, then I'd suggest that they are hugely ignorant of everything related to technology.
The matter of upgrading is even more applicable to software applications than it is to hardware. Oftentimes, software vendors stop providing support based on your current application version much sooner than based on the version of hardware upon which the application sits. We have multiple vendors that have upgrade cycles that render applications unsupported within 18 months. The reality is that you cannot simply "stick with what works" if you're attempting to mitigate any sort of risk.
Also, asking questions like "why not just use Skype" completely ignores complexities and requirements of identity and access management, ease of systems' integrations/use, and security in general.
In the words of Da Mayor - "those who tell don't know, and those who know won't tell"
With that all said, I do believe that you are right in that the problem is one of communications. IT needs to treat the business as customers, and in doing, work to understand business needs and then strive to effectively meet them...