I bought a Chumby as a Christmas present for my wife but could not refrain myself from opening the package and use it for a while... just to make sure.
so; here are my first impression ...15 minutes test.
it is very easy to set up: I mean it, set up was a breeze
the hardware is cute; I really like it; you can hug it, squeeze it, shake it... the power cord is a bit of a pain but I can live with it... for a while
I would really like to see some kind of cradle for the nest generation; something I could just put it on and let it charge.
the interface is not as easy as I would like (note that this really was a 15 minutes test); I wish I could jump from one widget to an other based on tapping on the screen or jiggling the thing around instead of having to set a time or change channel.
for future hardware; I would really like to see a camera on this thing; along with a hardwire disconnect for both the microphone and the camera (you DO NOT want to hear or see me snoring).
also a GPS chip would be welcomed; and I would have liked the squeezy hardware to be pressure controlled (think pressure in a bladder) instead of the mechanical thingy currently used.
as far as widget are concerned; here is my current list:
a pandora widget (I need that while baking... as in cooking)
a wwitv widget (yes I want to watch the ABC  or the Woodworking channel feed on a 3.5" screen)
a clock widget that comprises alarm options (to wake me up)
an internet radio widget (I do need WWUGA in the morning)

otherwise; this 15 minutes test just left me drooling over the possibility of this type of platform.
I think this is the start of a new type of appliance; the internet type...

keep up the good work