How to sync Music to 160 GB iPod Classic version 2.0.4 PC

My thanks to you at the outset.

I have a 160GB iPod Classic version 2.0.4 PC from 2007. It was a beauty.

All I want to do now is to store audio lectures and music on that old iPod Classic and listen to the content without needing wifi.

The PC version hosting iTunes that was used to store audio files on this Apple device died 4 years ago.

Last week I decided to add more data to the iPod Classic.

That is where things went awry.

I tried to get help on using the iTunes on my later windows 10 PC.

The first Apple Customer service person tried to and ended up suggesting a reset on the Apple device.

Result: The iPod Classic now has no music. When plugged in, the iPod Classic connected and immediately disconnected with an error message complaining about the drive.

So I bought a new connector from Apple.

Since the iPod now was in reset state, I decided to update the content that would go on it.

On my PC, I created a new directory called consisting of a set of subdirectories of audio files to populate the iPod Classic.

The 2nd Apple customer service person upgraded the iTunes to version 11.a.b (sorry it happened too fast). The iTunes on the PC showed the old set of files. Trying to open them failed.

They had to create a new iTunes folder. ITunes1. To that folder, they “dropped” the AudioForIPod into iTunes1.

They connected the IPod Classic and started Syncing.

That is when things got crazy.

Every so often the system complained with an error 50.

I deleted that file; then Physically pulled out the connector and replugged it into the iPod classic to continue the sync.

Repeated this hiccup process a lot.

Now the syncing was random. Not by the directory setup. There was no way of telling how far along I really was. Or where in the content I really was.

Finally, the drive complaint and then device is not recognized by iTunes.

All I wanted to do was to store audio lectures and music on the old iPod Classic and listen to the content without needing wifi.

Is this iPod classic now useless? I hope not.

Please can someone Help!

I’m not sure if the tag is correct.

Thank you!