I have a Chumby Classic (just one, not ten of them) that has had a similar problem for quite some time now. When I go through the network settings, it sees my network, obtains an IP address via dhcp, appears to be connected, but says that chumby.com is unreachable. Same thing when I enter the network information manually.
Occasionally, however, it will connect and work OK. It seems to disconnect/reconnect intermittently, as I'll catch it with the Star Trek clock displaying at times, and at other times the default offline clock is up (though it spends the majority of time not connected). This actually started happening a couple of years ago, and I'd given up on it and left it unplugged until a few weeks ago when my Chumby One (which had no connection problems) died and I started playing around with it.
I've got a couple of laptops, an android tablet, a droid phone, an iPhone, a wireless web cam, and a Grace Mondo Internet radio all routinely connecting without issue, so I'm reluctant to blame it on my AP.