I can download to my mac...but not transfer to Ipad2 or AppleTV.

Over the last 3 weeks, when I download a tv show to my Mac from iTunes, it plays fine on my mac. When I try to transfer it to my ipad2, it says "Video cannot be played on ipad"
And when I try to play this video on my AppleTV, it will not play either... it claims my computer is not authorized. I have already deauthorized and reauthorized my computer, rebooted my ipad, updated my software and all of the little suggestions people like to make... this isn't my first day. But I am truly at a loss as to why things aren't working right...
If I download the video from itunes to my ipad and transfer it to my Mac... it all works just fine.
Suggestions?

I have reports that are generated by a medical device that I can plug into my mac via USB directly from the device, and the information in the device transfers to the computer where I can view it and/or edit device information. When I try attaching the device to my iPhone it doesn't communicate at all.

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