If you used iTunes Match, you could then have all your music available to you on your phone by streaming or to download at will. You can still keep everything you have on your hard drive/iPod, but also have cloud versions available to you. No loss of control, probably better sound quality for streaming than what you currently have on your pod.

Thanks for the fast responses, guys.  This is a bit of an emergency for me!  Zig, I listen to my tunes on an iPod Classic (’cause I’m a classic!) on headphones and on a Bose iPod speaker stand.  I mostly listen to music on headphones and would like to preserve the option to keep my entire library mobile (my commute is an hour one way).  

Allegedly, there are people out there who are selling refurbished iPod Videos with 240GB hard drives in them. Unholy abortions, these devices, but they can be found. I have even heard tell, in anxious whispers, stories of a mythical iPod upgrade kit available on eBay.

But these options only delay the inevitable (and at cost).

JaPaBo, I’m sure we can help. Refresh my memory–how do you listen to your music? Is your Pod docked to the Wave Radio? A better option than getting another laptop is getting a large external hard drive (1 Tb will cost you only about $80 or less), hooking it up to your current laptop, and then connecting that to your radio.