[THE WIZARD]

I am totally new to smartphones and tablets so am desperate for help on so many things to do with them !
My husband & I have Samsung phones (different models) and I've just bought him a SGT 2 10.1

I believe I need to download Kies onto my PC in order to update the phones from Gingerbread to Jellybean.
My first question is : if I download Kies will it automatically recognise that they are 3 different devices when they are each plugged in? If it doesn't and everything that gets added to Kies then gets downloaded on to all 3 devices, will I be able to delete what I don't want from my device without it deleting from my husbands devices?
My other question is my husband would like to have music from his iTunes Library on his Tablet. How easy a task is that to do using Kies? I know I first have to make a playlist in iTunes as he has so much music on there before I attempt to drag and drop it into Kies but am worried I may loose some of his music if I get it all wrong. If the drag and drop works does the music go onto his internal SD card that came with the phone or are you offered the choice of adding it to the external SD card (32 GB) that we added for such a purposed.
Hopefully somewhere on the DIBB I know there are expects in such things, please God they read this thread
Thanks for any help
Pat