The biggest challenges with Windows in education currently are how long it takes to set up and log into user accounts, and how much time is required for maintenance to keep the OS and apps updated.
Van - how does your organization deal with these issues? From what I understand, ease and speed of log-in and servicing is one of the biggest reasons why many schools choose to deploy Chromebooks.
I think we have a few things going for us that helps:
-we have centralized IT (I know a lot of districts are on their own and cobble together an IT team)
-we have a lot device types, but mostly we have reduced our labs away from laptops/desktops to thin clients. The remaining devices are all Windows 7 or newer and are centrally managed in terms of antivirus etc.
So basically setup was not a problem. Devices are joined to the network and we have single sign-on so logging in isn't a problem. External devices can connect to our limited (and monitored) internet but not network resources. Maintenance is an issue for sure, although its hardware maintenance mostly and that doesn't go away with chromebooks and tablets.
On the subject of things that don't go away with chromebooks and tablets: Even if the updates are done automatically, they can still wreak havoc on existing processes and software we use. For example, a Chromebook update in the middle of a testing window made our secure browser inaccessible, meaning we couldn't test students on those devices until we could figure out a workaround. Keeping apps updated is no easier on those devices either because custom apps get updated on Windows first most times, and updating Office is no longer an issue now that it's cloud based.
Finally, the "ease of use" argument might make more sense once our workforce becomes younger, but older folks and folks my age (30's) and even late 20's have no problems using Windows PC's. In fact, many of them prefer PC's to devices, ESPECIALLY for productivity. Don't ask a principal to type anything on a damn ipad. Don't ask a coordinator to use a chromebook, just give them Windows with Office and Outlook preloaded and they're good to go. Now, when my daughter's generation grows up, things will be easier. She isn't as comfortable with PC's, but that's still a ways off.