I finally also bought a Jitterbug and couldn't wait to test it.
I plugged it into my USB port and plugged in the cable with the DAC.... hmm nothing. Windows will not recognize my Device. Tried a different port, same problem, tried the last available port which supports a higher current - the DAC was detected but with the standard cable i had an awful distortion! I tried another 28AWG Cable and the device then played "normally".
So i researched a little bit and then decided to open up the jitterbug and have a closer look. I saw some choke coils on the PCB and removed the last one on the 5V line - bridged the connections and tried plugging in my DAC again... it worked on all ports !!
So what i will do next is.. i order a "better" choke coil früm Wurth Elektronik (WE-SL5) and will try my luck with this one. I also remove the USB connector and will solder a 20AWG sync+data cable directly to the PCB with silver solder and keep the cable as short as possible (around 10cm).
I will update you with the progress.
For those who had good luck with their device from scratch - good for you, but at least i now have a new project to mess around with