Using playlists to deal with full iPod

Many apologies if this is a stupid question, but i have searched this forum and the iPod one and not found an answer.
My 40GB is full, and I'm looking for a way of doing pretty much what the shuffle does, i.e. autofill so that each time i dock it I'll get a different 40GB selection from the library. I also want all my playlists available, but not necessarily in complete form, although it would be good if my 'random' 40GB selection always included stuff added in the last month. Basically I want a random selection of my lower rated songs, equivalent to whatever amount my library is over 40GB, to drop off each time I connect.
Believe me, I wanted to use this and the fading battery as an excuse to get a new 60GB, but i'm going for the replacement battery and playlist option instead...much less fun, but cheaper!
Cheers
Jon

Error 13, 14, 35 and 50 (or -50)
These errors are typically resolved by performing one or more of the steps listed below:
Perform USB isolation troubleshooting, including trying a different USB port directly on the computer. See the advanced steps below for USB troubleshooting.
Put a USB 2.0 hub between the device and the computer.
Try a different USB 30-pin dock-connector cable.
Eliminate third-party security software conflicts.
There may be third-party software installed that modifies your default packet size in Windows by inserting one or more TcpWindowSize entries into your registry. Your default packet size being set incorrectly can cause this error. Contact the manufacturer of the software that installed the packet-size modification for assistance. Or, follow this article by Microsoft: How to reset Internet Protocol (TCP/IP) to reset the packet size back to the default for Windows.
Connect your computer directly to your Internet source, bypassing any routers, hubs, or switches. You may need to restart your computer and modem to get online.
Try to restore from another known-good computer and network.
"Error -50," "-5000," "8003," "8008," or "-42023"
These alerts occur due to timeouts or conflicts trying to write a file during download.
If you encounter this issue while accessing iTunes Store:
See iTunes 9: "One Moment Please" or "Error (-50)" message when accessing iTunes Store
If you encounter this issue while while downloading something from the iTunes Store:
Delete your iTunes Downloads folder, located in:
Mac OS X:
  ~/Music/iTunes/iTunes Media/Downloads   Note: "iTunes Media" may appear as "iTunes Music. Also, the tilde (~) refers to your Home directory.

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