I am playing with converting some stuff to mp4 for a friend with an iPod with Video and so was testing some of it on my 442. Most of it plays fine, but it appears that anything longer than 1 hour will not play. I have not done a lot of testing, but I have several files that are 40 minutes and they work great, but I have other files that are more like 1 hour and 40 minutes and those say "Unsupported" and will not play. However, they do play just fine on the iPod.
I am encoding them at MPEG-4/320x180/16:9/768k in the Videora iPod Converter 0.9[1] as they are 16:9 content. That is a custom setting I made for the 16:9 content in Videora.
Anyone have any other experiences, or should I do more testing and put something in bugzilla?
[1]
http://www.videora.com/en-us/Converter/iPod/