I haven't researched them in depth, but for me it's probably going to come down to the fact that the Roku does WMA DRM. I've got a Yahoo Music subscription for my Carbon, and I'd like to listen to those songs somewhere besides the Carbon or my computer if possible.

The Squeezebox had a bit of an edge for a while because it's got integrated ethernet<->wireless bridge functionality. However, I just recently bought a 2nd WRT54g to bridge my networks together, so that's no longer a plus for me.

I'm right there with you on the video out thing, though. I'd given some thought to Roku's PhotoBridge player, but that's the same problem in reverse, since there's no on-device display. What I want is a device with a high quality VFD display, compatibility with any audio format I might want to use, logical and sensible navigation and searching of songs, a choice of server software, video out with a well designed and good looking UI for the TV, kick-ass visualizations for both the TV out and the VFD, integrated ethernet and wireless, and digital out. Oh, and for less than $100. What's so hard about that?