Windows – Restore an iPod nano (1st gen.) to older firmware version

Try this thread, it's the first one I've found that's seems to be on to something:

Essentially, iPod likes it's Audioboos in one large file. This means you'll need to merge your multi-file Audiobook into one large file and convert it into the .m4b format. Ipod will then keep track of your position in the file, but if you want chapters you'll need to set those too.

Luckily we're not the only ones facing this problem and tools exist for performing both operations.

There's a Freeware tool called: Chapter and Verse that can be found on lodensoftware.com

If you're willing to pay for the privilege, there is a shareware application called: Chapter Master that will place chapters in the kind of one long file Audiobooks iPod likes.

Mind you, you'll first need to convert your MP3s to M4A or M4B. This can be done through iTunes, as well as through a freeware application called: MP3 to iPod Audio Book Converter.

You'll have to Google these programs, the system won't let me post more than one link.

I hope this helps,

I've never done it, but I found some decent looking instructions here:

For Windows:

1 Connect iPod nano (5th generation) to your computer.

2 In iTunes, click iPod in the device list.

3 Click the Summary tab.

4 If "Enable disk use" is not checked, select the checkbox and click the Apply button.

You will now be able to copy recorded videos to your PC.

Using Windows Explorer or My Computer on your PC, the iPod nano will appear on the computer as an external disk with the same name you gave the iPod during the initial setup in iTunes.

The DCIM folder on iPod nano stores your recorded video. You can copy this folder to your computer so that you can view the video on your PC, or to back up the video files.

Once the recorded video is copied to your PC, double-click on the file to watch the video using QuickTime or Windows Media Player. See the documentation that came with your computer for assistance.

For Mac: (using iPhoto)

To copy your recorded video from your iPod nano to iPhoto, you first need to make sure the "Enable disk use" checkbox is selected for your iPod within iTunes.

1 Connect your iPod to your computer.

2 Open iTunes (version 9 or later).

3 Select your iPod in the Source pane.

4 Select the Summary tab.

5 Enable disk use and select the Apply button.

Import your recorded videos from iPod nano (5th generation) to iPhoto

1 Open the iPhoto application if it doesn't open automatically.

2 Click iPod in the iPhoto device list.

3 Select the video or videos to import. Click Import Selected or Import All.

4 After the video or videos have been imported into iPhoto, choose either Delete Photos or Keep Photos when prompted to "Delete Photos on Your Camera." Your recorded video or videos will appear in your iPhoto Library under the section for Events and Photos and in the Recent category for Last Import.

To watch the video in iPhoto, double-click the recorded video.

Hope that helps.