I run a Squeezebox into a lower end DAC (soon to change, but for now a Musical Fidleity X-DAC) - my Marantz 8300 (through the DAC to keep it fair) sounds better to me - but it is close - darn close - close enough for me to use the Squeezebox for most of my listening - the Marantz only gets turned on these days for SACD playback or for serious redbook playback as the Marantz DAC is superior to the little X-DAC.
Ok - getting music on there - not so easy - especially if like me you use one comptuer to rip your music and another (in my case, a low-end desktop PC running Solaris) as your music server.
I guess the simplest way would be to use a Windows box as your music server running SlimServer and iTunes - then just configure SlimServer to serve up your iTunes library. In this case - probably quite easy. Certainly a lot easier than having to FTP files around as I do in my case.
Make sure you rip your music in "Apple Lossless" though - iTunes is preconfigured to use high compression AAC, so change that in the iTunes preferences the first thing you do.
Of course, the ripping process is tedious - especially if you want your tags to be correct and consistent. Eg. I've got a few funky/jazz albums by the *SAME* artist and for "Genre" I've seen it automatically display "Jazz", "Funk", "Acid Jazz", and would you believe it, "Pop". Manually changing all of this takes time - if you demand it to be correct.In other cases I get bands listed with and without "The" and with "and" and "&" used interchangably. Of course, this doesn't matter so much per se, but it is really annoying when you're trying to find a "Vika and Linda" album only to realise that particular album (unlike the rest of them) is listed under "Vika & Linda".