I cannot get my purchases on iTunes to download to my nano (version 6)

Everytime i purchase something new on iTunes and attempt to get it to my Nano, it will not download. The only way i can get these items to sync is to sync my whole Nano, thus loosing anything not purchased through iTunes. I have to copy the files back off my Windows machine after i re-synched iTunes which includes my new purchases. I've contacted Support numerous times, they've never provided anything that has worked. If i attempt to drag an item and drop it to my Nano, nothing happens, it shows my device as being available to add it to, but doesn't do anything. I'm seriously to the point of completely disbanding iTunes and Apple on this, I'm using a Nano on a mini-Mac at their store and it will not synch automatically??? Any ideas would be appreciated.

They are not all on iTunes, I copied some over from my old Droid device when I bought the Nano,. It was my understanding that there isn't a way to get those into iTunes. Does having initially setup the Nano on a Windows machine have anything to do wish this? I've switched to a Mac mini as the Windows machine is on life support. I never had issues downloading from the Windows pc.

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They are not all on iTunes, I copied some over from my old Droid device when I bought the Nano,. It was my understanding that there isn't a way to get those into iTunes. Does having initially setup the Nano on a Windows machine have anything to do wish this? I've switched to a Mac mini as the Windows machine is on life support. I never had issues downloading from the Windows pc.

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I cannot get my purchases on iTunes to download to my nano (version 6)

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