I use the Bel Canto DAC2 with a Stereovox digital cable and I have never had a problem with signal dropout. I have owned the DAC2 for about 2 years. I am using a Rega Planet as a transport.
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Check to see which DACs work with the Apple Airport Express. Some drop out and some do not. I think it is because of the lack of a clock in the airport express. I read this in the stereophile review. Try one that does not. Also check with Olive. They may know what works best.
BTW, how doe you like the Olive. Can you use it without a DAC. That might make the most sense if it sounds decent.
I think I responded to your older thread before, or may be it was somebody else with a similar problem, but in any case, I suggested a Virtual Dynamics NiteII digital cable, with which I had none of the signal drop outs I experienced with other cables and DAC2. These drop outs are caused by switching fluorescent lights on and off somewhere in the proximity of your system. Well, besides the signal problem being solved by NiteII digital cable, the sound of the DAC2 was taken to a completely new level. I have not heard this dac sound that good with any other cable. Before you ditch the DAC2, why not give it a try with Virtual Dynamics NiteII cable? You may get the signal problem solved by buying a different dac, but the sound of Bel Canto DAC2 is pretty tough to beat, especially if it runs with NiteII cable.
www.fatwyre.com has a huge lending library of cables and you can borrow the NiteII from them. They charge 5% of total cost(last time I checked) so it will run you about $30 to try it. Besides, the money is not lost. They will count it towards your future purpose. Whenever and whatever it may be.