Been fucking around with the Archos a bit. First off deleted a few things as I only had about 1.5 gigs of free space left, and will be sure to have a lot more available in the future as that might have played into things.
I tried playing the file a few times, some times I got static, others another kind of static, one time an error message, and now I'm listening back to my show. I'm praying I can listen back to the whole thing. So then even if I can't do a proper digital transfer, I can run the archos output right into my soundcard as if I was doing a casette transfer.