Sam,
We have a hands-off policy at Wenona around onboarding and have all our girls connect their own devices each year, the IT Staff don't do it for them. They will assist but they get an angry look from me when they do it for them. Clear-Pass has made this process seemless for us.
We had some issues in the first year with their Java based app and Mac's not likely it but since turning off the Java client it has been pretty much flawless.
We have the odd issue on students constantly onboarding their device and ending up with 30+ certificates in their Keychain and WiFi gets confused of which certificate to use. Though a quick delete of the excess certificates and there good to go again.
Been using ClouthPath for years here at Wenona and wouldn't leave it any time soon, in fact I recently used it to build a Guest Access system which doesn't require a seperate SSID for guests.