Matt,
This was a while ago, so I hope I get it all right, but talking with Steve I recall him saying that he often uses a computer to audition gear, and that it is potentially the best source. A big theoretical advantage is that you can first run your CD, or other uncompressed data through error correction software, then once corrected, and played through a software player that does not add or subtract anything, the source does not have to correct errors so you get a more pure sound. Even new CD's can apparently have errors.
I am sorry that I did not set the playback software in my mind because Steve uses Windows and I use a Mac. I think foobar (sp?) was the error correction software. (correction...foobar is a player).

Another theoretical advantage beyond the convenience you have found of not having to worry about discs getting scratched or worse, is this: once properly corrected, you can get exactly what was intended from the data. There is no influence from the CD material, pressing issues, beam reflection or other error issues. There is also no other influence from a transport and its electronic signature.
Then there is the extremely low jitter from a hard drive. All theoretically very good stuff.
Alternately, like Randy brought up with his love of his source and from his quote from Steve.... Where Steve liked the latest Zen CD transport sound better than USB "if you find the right cable"... a good transport and cable may add sound we like!
When my ZDAC comes, I intend to experiment between using our laptop and my CD and DVD player transports. This should be fun.
I look forward to any information you come up with about software players and USB cables. You hear those who swear it is all 1's and 0's so the cable makes no difference, but then you hear those who swear they hear the difference in digital cables. Some of these are our trusted Forum buddies from this thread.
Since they make a difference from transports to DAC, it would appear they might make a difference from computers to DAC's too. May have to do with the perfection (or lack there of) of the transmission. Don't know, but I do know I can hear every minute change I make with my gear.
Let us know.
Also, I have run across several posts in this Forum about computer sources use. Can't tell you exactly where though.