I had the squeezebox and it was a nightmare. It never just worked. Logitech would update the firmware and break something else. Every time I turned it on, Id have to play with it to get sound. They have updated the squeezebox but I dont have any experience with the new model/system. Id be very leary of anything Logitech as IMO they have gone downhill in the past few years (ie. Harmony remotes).
A few months back I bought a Sonos Play 5 and was impressed by the sound and ease of use. I bought another play 5 and made a stereo pair and also bought the sub and the sound is incredible. Its also works every time, never had an issue. I recently got the Sonos Connect:Amp and a pair of the Hsu HB-1's and a VTF-2 sub for my computer room. Also have another Play 3 and Play 5 that I move around the house/garage. I have my Sirius/XM and Pandora accounts that play thru everything along with streaming MP3's from my server.
Problem is that Sonos is very addictive. I find myself wondering where else I can put a Sonos box. They are pricy but at this point in my life, I dont want to dick around with making things work. Every time I turn a Sonos box on, it works.