I've been using a couple of Roku SoundBridges for 5+ years now. Quality is exactly the same as CD with a lossless rip. The SoundBridge is long since out of production, and I may replace mine soon because they are limited to 16-bit/44.1kHz or 16-bit/48kHz and now I have plenty of 24-bit/88.2, 96, and 192kHz rips on my computer (I have to make 16/48 copies for my SoundBridges, and while they still sound great, I want full resolution). The Squeezebox Touch will play 24/96 stereo, but I'm holding out for something that can stream 24/96 5.1 channel and beyond. An interesting product is the Dune Max HD player, but it is more geared towards video and apparently doesn't play FLAC gaplessly (at the moment, anyway) unless you rip as a single file w/cue sheet.

A friend of mine thinks I should just get a new laptop with HDMI and call it a day. He uses MediaMonkey4 with WASAPI enabled (as I do) and connects it to his pre/pro and it plays nearly everything (no SACD...yet) with bit-perfect output (FLAC, BluRay with Dolby or DTS lossless, DVD-Audio, etc).