Just before we deployed our iPads in a Pilot Program, we Supervised them using the Configurator. In an effort to save time, we grabbed three brand new laptops (that were allocated elsewhere), installed Configurator on them and using USB hubs got them all ready to go. Or so we thought...
We missed the part that said that once Supervised, the devices could only be connected to the machine that was used to supervise them. Oh boy. Those laptops would be gone, the Configurator deleted and we'd be in a serious pickle. It was at that time that we also realized that the students would not be able to sync their device with their home iTunes account.
That had us wondering what to do about backups. Collecting the iPads once a month and performing backups was a possibility but a small tech staff plus teacher scheduling iPad time in class made that pretty difficult to set up.
We had to re-supervise the devices on a dedicated machine before handing them out and learned a good lesson. After we had a few screen breakages, we were able to back them up into the Configurator and restore that backup onto a replacement device. We discovered that this required quite a bit of housekeeping on the part of the student as they had to re-download all of their apps and recreate their folders.
We had the students set up iCloud on their devices after a couple of breakages just in case one broke badly enough to make powering it on impossible. We were pleasantly surprised to find that iCloud is the bomb! When we power up a replacement and restore from an iCloud backup, all apps are put back into their original state and back in teh proper folders. It takes a bit longer to prepare the new device but once you hand it off to the student, they are all set.
Another issue that we're dealing with is the Exchange ActiveSync portion of Configurator. Since this tool was designed for mass deployments of iPads, it is curious why Apple does not allow you to set this up to prompt a user for their name and password. You have to enter them manually. Oddly, the boxes you fill in say you should leave it blank to prompt the user, but apparently that only works if the devices is unsupervised. If supervised, you have to fill in those spaces. Such a total bummer.
I'm posting this info again to strongly advise that you carefully consider how you handle your deployment of devices.
