Managing/Updating devices with different versions of iOS

Hi
I help manage a series of Apple Devices in our enterprise many of which have not recentlyl been updated to "newer" iOS versions. A handful of tehm go back to 4.2/4.3/5.0
I was curious to know if there were any upgrade recommendations or expectations to 8.1. Does it need to be a staged update for the oldest versions, is it even possible to do a staged update? Are there considerations that need to be made prior to encouraging users to backup and upgrade to the latest iOS?
Thanks in Advance.

Actually, on looking closer:
When I open the .nef files (double click from Bridge), CR 5.5 launches.
When I open .jpg files (CR icon on toolbar or "Open in Camera Raw" menu option, also from Bridge), CR 5 launches.
How / why would I have two versions - and with different menu options?

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