Unable to load all MP4 movies located in iTunes

Question

For some reason, I am no longer able to load all of my MP4 files to my iPod. They are all located in the iTunes video folder, but only about 18 randomly get loaded. Previously, I had over 24 MP4 files loaded, but since I have gone over that number, I can't even load that many anymore. I have ~20 GB of MP4 files, ~11 GB of MP3, and maybe 500 MB of photos that should be on my 60GB iPod. There is an additional 20+ GB of free space, so why won't they load? I reformatted the iPod, keeping it in version 1.0. I'm using iTunes 6.0.3.5.I reloaded iTunes and the library about a month ago. The only other quirky things that happens with it, is that it doesn't always shut down when I hold down the 'play/pause' button. Sometimes it takes 4-5 times to shut down. And, when its done updating, the only way to get rid of the 'do not disconnect' screen, is to shut the whole computer down. Does anyone have any suggestions? PLEASE
Generation 5 - 60GB Windows XP Pro
  Windows XP Pro  

Answer 1

I have almost the same problem, I currently have 67 movies on my 30Gb. But there are 4 movies in my library that won't go, you can watch it start to load and then it locks up and skips on to the next one. I've reset it many times, and have the current version of itunes and in my ipod. I've ripped and converted the movies all the exact same way and don't understand why the 4 won't go. I convert them with a psp program, I thought about letting itunes do it but it takes so long and the rest of them work fine.