HT203180 purchased movies not re-syncing

I have been having this problem for a few months, and is now getting ot the point where I am going to throw my phone and laptop through a window!
Problem is as follows:
I have recently downloaded some movies from itunes directly onto my iphone 4.
I noticed there was an update for my phone, so i have updated it fully tonght.
The movies have now gone into my itunes, but will now not re-sync onto my phone.
There is enough space on my phone
Other movies will sync (some of which have been purchased the same way, and others have been taken from DVDs that have a digital copy - following the instructions).
I am a mac user, and have only been experiencing this since January this year. I have never had any other problems with itunes and syncing at all.
I have made sure that all of the items are compatible, and so any help that involves 'create ipod/iphone version' will not help - I have made sure of this, and cannot actually create this version, as they are already the correct version.
I just don't understand why some will transfer and others won't.
When I select 'manuallymanage music and videos when syncing, it makes no difference. I will then select the movies in the iphone tabs, and at the top right, it will say that I have selected a number of videos, but the taskbar at the bottom showing what will be transferred to my phone does not move at all. It will only move when I select certain videos.
I have checked the file locations, and they are all within my itunes folder, so I cannot understand what is going on.
Any help will be greatly appreciated. I feel there may be a trip to an apple store coming...!!

If it's a newer movie, I fear we aren't going to be able to download anymore. I sent Apple an inquiry, I think any movie that will be available in the cloud will not sync on an iPod Classic. Two recent movies I purchased, one through iTunes, an HD version, and one at a store with a digital download code, will no longer sync to my Classic, but it will to the phone or iPad. Not a happy camper with Apple at this time!

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Message was edited by: emeraldrina22

Which version of the firmware do you have on your iPod? Is it the latest (1.3), or earlier? I ask because of the information regarding Fairplay version 2 versus Fairplay version 3 on this website:
http://forums.ilounge.com/showthread.php?t=231582
"1.3 firmware has bug fixes and also an updated bit of code to play anything from the iTunes store that has a fairplay version 3. Most stuff on iTunes has Fairplay version 2, but some more recent videos have version 3. If you arent' downloading a lot of DRM'd content from iTunes, it likely isn't critical, but there have been no major complaints about the 1.3 update. At least compared to other updates. for instance 1.2 WAS a shoddy update. They pulled it. 1.2.1 fixed it... But nothing much else added to 1.3 if you are having no problems currently and don't have any fairplay 3 items in your library."

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