The upgrade has nothing to do with the ability of your users, average or not. As already stated, you control OTA updates by policy. Policy is either on or off, no in between. You'll need to decide how to control this. You could enable two policies to your users, one which allows upgrades and one that does not.
If you do go the OTA route, you'll need to jump through additional hoops. The OTA version will need to be carrier approved and the current version that your device will be upgraded from will also need to be the version your carrier put on their to begin with. If you follow these steps, you will not need to have the user reactivate. Good luck.
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I'm actually lost...
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