Flaws in this chain?

kahlenz I think you hit the nail on the head from everything I have read about jitter on engineering and pro audio sites it's another blown out of proportion worry any jitter produced is outside the audible range and if you are using a well built dac no need to concern yourself with it. 

listen to the wind blow, down comes the night
running in the shadows,  damn the DAC damn the interconnects
break the silence, 

Yes, jitter was the #1 issue which is why I'm glad they have figured it out in well designed modern dacs that have been made in the last 20 years or so.  Actually longer than that but I believe dacs have improved in the last number of years but that's just a belief if I had to pick a well designed dac from the 80's from a newer one in a blind test I doubt I could. I have listened to files that have jitter in them which can be found at various sites like hydrogen audio, AES etc.. and I have never heard jitter in my system.  So if I don't hear it, I don't worry about it. 

Sound on sound has a good article "Digital problems, Practical solutions". In the section on jitter the bottom line is it just isn't a  practical problem anymore and this article is 10 years old. If you are slaving multiple A-D converters then use an embedded external clock.