I've seen several other instances through my travel through Google and the forums of people having trouble adding mp4 files to iTunes and getting no error messages. However, I've been using Videora converter, and I've converted several files of the same file name length, format, and roughly the same size and successfully added some to the iTunes library, but not others. All the videos play just fine in media player classic, vlc, and zplayer. Any suggestions?
Continue to use winamp. Know that you are losing any spark of life in your audio files when you convert lossy to ANYTHING. Use a third party tool to sync videos. Winamp can play most formats nativly so you can keep your quality and hear the music.
I am just making a wild guess that itunes is suspicious of the tunes you tried to import. It will attack without warning if it thinks you have been naughty. I would be very careful! Make sure your ipod is backed up. It does not even have to be running to do you in.