Why is Itunes taking so long to update Ipad Moives

Itunes is taking a long LONG time to update a simple 300 Mgb TV show from my Windows 7 Ultimate PC to my IPad? Both have the latest updates. It used to be easy and take a very short time.
Is Apple intentially making it hard to work with Windows in hopes of moving me to Apple products only?
This is very frustrating. I can't even make my Apple TV sync with my Windows computer on the same network.

I have this same exact issue, however only with music. It happens when files are added in anyway: dragged, automatically added, opened from safari.
I have Mountain Lion, a new MacBook Pro with Retina, and iTunes Match turned on. I have a feeling iTunes is trying to match/upload the songs first. I've just added 10 songs, iTunes said they were copied over but they don't show up in my library but I can see the cloud icon "working".
EDIT: That's not the reason, the songs finally showed up but they are still waiting to be matched.

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