I wouldn't say it's a toss-up. The main differences are that the Squeezebox has a MUCH nicer UI than the SoundBridge does and is capable of working with a lot more formats, while the SoundBridge can work with Microsoft's PlaysForSure DRM (which is used by Napster, Yahoo, and Rhapsody).

(Well, and also that the Squeezebox is a device that makes attempts at being a serious audiophile source, whereas the SoundBridge M1001 can't even pass an unaltered 44.1KHz digital bitstream. And the Squeezebox supports G networks instead of just B ones.)

I bought a SoundBridge to replace my old Squeezebox 1, and hated it intensely. Its UI was basically competent in that it was comparable to the one on my Dell DJ30 MP3 player; but compared to the Squeezebox, it was slow, awkward, and painfully frustrating. I can see how somebody who'd never had a device like this would like the Roku -- it's far better than a CD player -- but if you've used the Squeezebox, it's obvious that the Roku is missing the spit 'n' polish.