I'm experimenting with the SqueezeBox right now. I use EAC to create FLAC files on the hard drive. My computer is in a remote room, and I've hooked it to the SB with ethernet cable. I started with a wireless connection, and as far as I could tell, the sound quality was the same, but everytime I used the microwave, it interrupted the wireless connection....so if you don't plan on snacking while listening to music, wireless would be fine.
The internal DAC on the Squeezebox is just average,and has a rather compressed sound, not a very full soundstage and lacking in dynamics.
However, going to an outboard DAC improves the sound significantly. Right now I'm trying a Bel Canto DAC2. Sounds pretty good; decent soundstage, good extension although lacking in the bass. It's an enjoyable sound quality, but not comparable to my GNSC modified Wadia 861, but I wouldn't expect that from the Bel Canto. I'm going to try a Benchmark DAC1 next.
My preliminary opinion is that the SB does a good job as a "transport," and the ultimate sound quality is really a function of the DAC you mate with it.
It is a lot of fun having your entire digital library at your disposal via remote control.....don't even have to get up to change CDs ;-)