Have you checked the resolution? iTouch 3g can only play SD. while 4g can play pretty much everything.
I know this is old, but for the original question if it hasn't been figured out yet: What I always do when I open iTunes is click the x to make it stop syncing and backing up. What happened once was that I did that, and then when I tried syncing a video to my iPod, it would show up under movies in grey, and the info for my ipod would say it was taking up that space, but it wouldn't actually sync. What I did was unplug it and then plug it back in and let it do the 4 steps it does when you plug in an iPod. After that, the video synced normally. Hope this helps someone!
Syn. said: ↑ I know this is old, but I typed in on Google that my videos won't sync. I then found a solution to those still in need. Have your video highligted then up at the top on the bar, click advanced then create iPod or iPhone version. This should take some time but it works."Thankyou so much, this is the only post that has really helped" I tried this and at first it didnt work. Then after converting it I checked my iPod/device under the movies tab. I then realized that I hadnt checked the movie before trying to resync my ipod. After I checked it and hit sync again it worked! Finally an answer!! Thank you so much Syn!