I have a 30GB iPod and about 6500 songs. This is roughly 500 CDs, or about 1/40th of your collection. Performance got a little sluggish on my icebook, but it was OK. The UI was straining to handle that much data, but again, it was OK. The real question is what other choices do you have, short of writing your own? A lot of music management programs are designed to shuffle a (comparative) handful of CDs to or from a flash device One thing that you can do with iTunes that should work just fine is to have multiple libraries (e.g., Rock vs. Clasical vs. Showtunes), which helps keep the total size down. Craig