Welcome! Looking at recent ebay auctions, and guessing which one is yours, I'd say you did not pay too much. The 60GB model went for well over twice that originally (of course, for about 2 weeks it went for half that, but that was a strange time ).

I'll also vote EAC/lame. I prefer MP3 Tag Studio, though, for fixing bad tags. I believe you can also set EAC up so that you can have it quickly rip all your CDs, then leave it going unattended while it encodes the MP3s. This is very useful when you've got a lot of albums.

Also, like everyone here, I'd recommend upgrading to the latest software for your empeg and PC, though to answer the question I think you're asking in your post, it's not necessary to do it before you load music onto the player.

So again, welcome to the community, and congratulations on one of the best purchases you've ever made!