I had similar trouble with some LC AAC m4a on my old iRiver players, which would sometimes just skip the files and other times would hang on very high bitrate m4a, especially large files, and force me to do a hard reset. Most of the files in question would play fine on a newer player with more powerful CPU i.e. Sansa Clip+ or Fuze or Rockbox as an Application on an Android device, but some would fail to play even on these relatively powerful devices.
I was able to solve the problem by hinting the files with MP4Box
http://gpac.wp.mines-telecom.fr/mp4box/ "MP4Box -hint <your_file>"
basically optimizes the file for streaming (at the cost of slightly increased file size) and this seems to also make it easier to read/decode for very low power devices like an iRiver H140. Your iPod is even less powerful but it might be worth a try. MP4Box is available for Windows, OS X, iOS, Android and is in the repositories of Debian and similar.
If you run Linux/BSD/Mac then this script might be helpful in avoiding hinting files which are already hinted (they get bigger each time, so it's best avoided). I set it to ignore all except suitable m4a/m4b/mp4 files so I can lazily run it on directories with mixes of audio and cover art and text files without error messages. It writes an optimised temp file to /tmp instead of in situ, and then overwrites the original. That seems odd but is noticeably quicker than default (two writes to disk in situ) when the file resides on a slow disk (probably with very fragmented file system) such as is commonly found in ancient hard disk personal players.
#!/bin/bash
#hint_m4a
for i in "$@"; do
shopt -s extglob nocasematch
if [[ "${i##*\.}" == !(m4a|m4b|mp4) ]] ; then
continue
fi
MP4Box -info "$i" |grep "Streaming Hint Track"
if (( $? == 1 )) ; then MP4Box -hint "$i" -out /tmp/"${i##*/}" && \
mv /tmp/"${i##*/}" "$i"
fi
done
If your files are from iTunes they are already be optimised/hinted so there's not much you can do. Most of my problem files are LC AAC I've muxed with ffmpeg and need hinting to make them playable in RockBox. If you run Windows and prefer a graphical app I know that dbpoweramp converter can optimise/hint m4a.