All I'll say about digital vs. analog is that if have access to a vacuum tubed guitar amp (like say, a Fender Twin or something comparable) and use some alligator clips to attach the input guitar cable to a pair of butchered iPod headphone jacks, you are in for a TREAT.

I tried this once, and even with the mono output, I was blown away by how good it sounded. It was a little noisy because of the impedance mismatch of my ham fisted hardware hack, but it sounded warm and thick and full like you've never heard, like giving a down pillow to someone who's only had sponge foam pillows. Even newer digitally created music like Fatboy Slim sounded better.

It made me think of how those old Rock-Ola or Wurlitzer jukeboxes might have sounded.