First off, anything fed to the Benchmark DAC will sound as good as anything you can buy, so don't worry about sound quality. Or jitter, for that matter. The Benchmark can fix the worst bitstream you can throw at it.
I would advise against the Airport Express if you can help it, however. WiFi is subject to interference, and won't necessarily play well with your microwave, cordless phone, etc. Better USB out to some converter that can hook up to the Benchmark. I don't think you can go USB or Ethernet straight into the Benchmark, but M-Audio must make something that will allow the connection.
Finally, you do not want a 500GB HD. You want TWO 500GB HDs. One's a backup. Ripping 500GB of music is time-consuming. You don't want to have to do it a second time.
Even with the 2nd HD, you can't really spend more than $3000 on this without wasting money.
I would advise against the Airport Express if you can help it, however. WiFi is subject to interference, and won't necessarily play well with your microwave, cordless phone, etc. Better USB out to some converter that can hook up to the Benchmark. I don't think you can go USB or Ethernet straight into the Benchmark, but M-Audio must make something that will allow the connection.
Finally, you do not want a 500GB HD. You want TWO 500GB HDs. One's a backup. Ripping 500GB of music is time-consuming. You don't want to have to do it a second time.
Even with the 2nd HD, you can't really spend more than $3000 on this without wasting money.