Making a 2G Nano appear as an IPod Shuffle?

Automatic conversion of my lossless music to something smaller, AAC 128 is a feature that I think is quite necessary for the Nano. Obviously the Nano will not hold many songs at the lossless music file sizes. Duplicating my large music collection just for the Nano is far from ideal. I know and have used Windows music software which duplicates iTunes functionality while allowing for any size transcoding, but really would like a Mac solution.
1. Is there a way to make iTunes believe the Nano is a 2Gb Shuffle?
or...
2. Can anyone point me to software solutions for the Mac that can manage a music collection and accomplish the automatic transcoding?
Thanks everyone in advance,
Nano 2Gb (ver 1.1.1)   Mac OS X (10.4.6)  
  Mac OS X (10.4.6)  

What generation iPod Nano do you have?  I assume the Enable Disk Use option is ticked from under the iPod's Summary tab in iTunes?
If it's a 5G Nano, have you seen this article to help walk you through the process of copying these recorded videos to your PC.
iPod nano (5th generation): How to copy your recorded videos to a PC
B-rock

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