Audiophile Changer: Cool or Hopeless Compromise?

Hello again everyone. It is great to be back to this site. Having owned and sold a Levinson 31 (sounded fine but didn't REALLY do it for me) I am finally going back to analogue and perhaps, a SONY SCD-1.

For general every day listening of my 2-300 CDs, however, it would be wonderfully convenient to have them in a changer. Is anyone taking a digital output from one of these things and running it through an external D/A, for example an ARC DAC-1 or DAC2 with decent results? Which changer transport is the best? CD or DVD/multi? And can someone please explain "upsampling"? In my experience, I have never really been transported by anything digital. I am waiting to be converted but in the mean time, would just love to conveniently enjoy a few hundred CDs without getting a migraine or thinking that reading a magazine or watching cable would be more satisfying. Thanks for you ideas and advice. Happy holidays to everyone.