Honestly this isn't about analog or digital - it's about why the ipod - which is a noisy, tinny source in my opinion - sounds better than his turntable setup. Something is not matched correctly here - any decent amplifier and speaker combo should be able to showcase the ipod's lack of bass response, particularly with the god-awful sounding AAC codec that itunes tracks us. Are you listening to both sources in 2-channel stereo? Music, ESPECIALLY from LPs, is 2 channel only (forget quad LPs for now)and often sounds pretty poor when played back through 5.1. Next, and you were going to try this, what is your cart and can you get a different one? Next, have you tried a different phono preamp? Just because your receiver or Preamp HAS a phono stage doesn't mean that it properly matches the cartridge you are using OR that the RIAA EQ is correct.
AK