I use EAC to rip to FLAC. Then I use foobar2000 to batch convert to v0 mp3. So I have 2 libraries of identical music, one FLAC and one V0.
I think you should use V0. V1 doesn't save much more space in my experience. My whole library only shrunk by about 250mb. That was for ~3000 songs back then. You might as well go as high quality mp3 as possible, even if you can't tell the difference.
There has been a slight change in plans, When I said I was getting the ipod I researched more players and ran across the Cowon S9 and I've read some of the reviews and I even tried looking for the negative ones but there weren't any. I've already placed an order for it on amazon today, so it will just be my Zune and my S9. Is there anything such as problems I should be looking out for when I get the S9?
Nothing less than 256k. If you are planning to get better sounding headphones and stuff in the future I would say 320 at least. ALAC or WAV/FLAC is better but if you want to save space..... get 320/256.