My aunt won one and just threw it in the closet after not being able to hook it up, so she gave it to me. I connected it and loaded up some widgets on it. It's cool, but not $180 cool. It has an accelerometer in it to make some games on it a little more fun to play (otherwise, I can't imagine why they even bothered putting one in there) and some of the widgets are useful. The worst part, as was mentioned, is there's no totally-wireless funcionality. You can use the 9V battery, but that's borderline useless. I can imagine it might be ok if you want to occasionally disconnect the adapter cable to play a game or two, but it's really meant to sit on a desk of by your bed permanently. It also has 2 USB ports, something I haven't had a use for as of yet.
If this ever caught on, it would be cool. But for the time being, the amount of widgets out there is good enough to give the Chumby a "novelty" status. It would take a greater library of programs to make this seriously cool, and judging by the slow growth of the Chumby community, I'm not sure that's going to happen.