Purchased video from itunes online store will play in itunes but not ipod

It seems like this issue comes up for a lot of people. When I try to play the tv show I purchased from the itunes store on my 30gb ipod I get a grey screen, then it goes back to the menu. I've tried all the usual fixes- resetting, restoring, getting all the latest updates, etc. My video settings have "TV out" turned off as well, but that didn't help. Isn't there something else I can try? Does anyone know what the problem might be?
I also can't choose to convert the file for ipod. This solution has been offered, but seems pointless, since I got it from the itunes store. I would love to have a solution to this problem, before I vomit and crash into the floor.

I got my problem solved via the apple helpline, although it took a total of about five hours on the phone. First, I had to move up the echelons of representatives until I was actually talking to someone in America. It takes a long time for them to take you through all the trouble shooting steps and you have to explain several times that you've already tried everything.
The solution they found for me was lengthy and confusing, and I wouldn't try describing it in detail to someone else. It involved doing stuff on my computer: I had to put my video files into my "shared folder," create a new user on windows, log in under that user, plug in my ipod, and import the videos, which then worked. I don't know why or how it fixed the problem, but it's definately fixed. Before I did that stuff, they also had me restore my ipod. I would recommend calling the apple helpline, telling them you've tried all the usual fixes, and politely asking them to "elevate" your call, which means you are talking to the cream of the cream as far as representatives go. They should be able to help.
The representative told me that this problem is rare but more prolific on windows machines. So if you have windows and you're havings these problems, chances are your problem is similar to mine.

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HP 10 Plus; Android-Kit Kat; 1.0 GHz Allwinner A31 ARM Cortex A7 Quad Core Processor ; 2GB RAM Memory Long: 2 GB DDR3L SDRAM (1600MHz); 16GB disable eMMC 16GB v4.51
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TS3276 My o2 email account does not work when sending from my MAC it will accept incoming mail but not send it gives me a message that o2 account (offline) my mac I have no problem with my iPhone or mac laptop. any suggestions please.

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Hello, FayAnnR.
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Here is an article that I would recommend going through when iTunes indicates that a file can not be located.
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http://support.apple.com/kb/ts1408
If the media was purchased from iTunes, I would recommend deleting the missing media and either transfer purchased from your iPod or download them again via the third article below.
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tt2

Purchased video from itunes online store will play in itunes but not ipod

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