The first budget item to get cut in a city is usually the school budget. The same holds true for IT training in the corporate world. Many people in places of power are shortsighted and do not see the long term value in having smarter workers or citizens.
I have to disagree with you regarding younger generation workers "naturally turning" to IT tools. I have met many young workers who work hard and not smart. Email organization is a good example. Most young people do not use email very much at home or at school so why would they know any better about how to organize their email in the workforce? They use texting and social networking which are much less structured and not organization friendly. My IT department spends more time training younger workers to use the corporate tools available to them than we do on veteran workers. Veteran workers come in with more Outlook experience. They might have some bad email habits but they are less in the dark than younger workers.
I like your suggestion of the IT fitness check and will add that to my training tools.