This is precisely why I have heretofore avoided computer audio (other than an iPod into a Wadia iTransport to DAC). There seems to be no end of headaches and nothing causes more teeth-gnashing for me than computer issues. And I have not had to deal with USB cables, WiFi issues (if streaming music), backup drives, new software and a controller like an iPhone or Touch. This is all in addition to a normal music rig.
Seems many spend more time one these sites trying to sort it all out than slipping a shiny disc on a CDP and pressing play!
Perhaps in 2 or 3 years it will not all be such a headache. For example, 2 years ago one had to use a USB/SPDIF adapter because few DAC's could play well directly from a USB connection. Now we have asynchronous USB, etc., which appears to accommodate USB connections. Perhaps in another year or two there will be players like JRiver or MediaMonkey that are not such a bear to figure out and use. Fundamental problem seems to me that one is trying to convert a machine made with music as an afterthought to one where music is the main thought. In addition, there appears to be the prevalent fantasy tha some day there will be a ,ass of popular music available in Hi-Res. Unless Apple decides to do it, will never happen, and I do not think Apple sees the demand.
I am no Luddite and admire the people who have all this running and seem to enjoy it. But until it is a simpler process, I will stick with my old ways: transport to DAC.
Neal