Can't play songs on iPod 80Gb Classic.

Newbie to iPod. Former PC/Windows 2nd level support officer. Have brand new iPod bought duty free. Tried to load iTunes, but couldn't. Error message "The installer encountered errors before iTunes could be configured." It goes on to tell me to try later on. Searched on the error message in Google and visited several forums. As suggested, uninstalled Quicktime and purged registry of anything Apple with the exception of directly iPod related stuff. Puerged PC of ALL unnecessary files. Tried to install again with same result. One forum suggested Winamp as an alternative. Purchased and installed Winamp Pro. Getting to know the program, managed to rip and play a few tunes, but playlists weren't working. Purged iPod of all music (not control files!) and have successfulley ripped and synched about 600 songs onto the iPod in MP4/LC-AAC Encoder v1.28 format. Cannot play these songs on the iPod. It shows them as "now playing", but there's no movement on the progress bar or on the time countback. If I hit the play button and hold the iPod to my ear, I can hear the drive spin up, then stop. Can play files on the iPod on my PC. Hard drive must be OK, as I can synch to it.
Any suggestions much appreciated.

I was having similar issue. Songs would play to a specific point, then immediately skip to next song at same point in song everytime. All the songs I was having this issue with were MPEG Layer 1. I highlighted the songs in my library, converted them to AAC, deleted the MPEG-1 songs off I-Pod Classic, then re-loaded the converted AAC files to IPOD. That solved the problem. I don't notice any difference in sound quality either. I was worried they would be "re-compressed" by doing this, but can't tell any difference if they were. I have not loaded the new firmware, as I've been reading about all kinds of problems with it. The Classic manual on the Apple Support site shows this:
iPod classic doesn’t support WMA, MPEG Layer 1, MPEG Layer 2 audio files, or
audible.com format 1.
If you have a song in iTunes that isn’t supported by iPod classic, you can convert it to a
format iPod classic supports. For more information, see iTunes Help.

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