From the script you gave me to run it looks like on reboot the Chumby is picking the wifi access point that is at the top of the list instead of the one that was used last? I am not sure how the list is rank ordered but that is what it looks like to me.
It should be picking 00:0C:41:66:71:49 which my wifi access point (ssid: shyster2) but instead it is trying to connect to 00:1F:B3:05:F6:E9 which is someone else's access point (ssid: 2WIRE729).
Some more info from the script:
chumby:/mnt/usb# cat ifconfig.txt
lo Link encap:Local Loopback
inet addr:127.0.0.1 Mask:255.0.0.0
UP LOOPBACK RUNNING MTU:16436 Metric:1
RX packets:137 errors:0 dropped:0 overruns:0 frame:0
TX packets:137 errors:0 dropped:0 overruns:0 carrier:0
collisions:0 txqueuelen:0
RX bytes:14134 (13.8 KiB) TX bytes:14134 (13.8 KiB)
rausb0 Link encap:Ethernet HWaddr 00:1D:0F:B2:81:BC
UP BROADCAST RUNNING MULTICAST MTU:1500 Metric:1
RX packets:328 errors:0 dropped:0 overruns:0 frame:0
TX packets:28 errors:0 dropped:0 overruns:0 carrier:0
collisions:0 txqueuelen:1000
RX bytes:25458 (24.8 KiB) TX bytes:2046 (1.9 KiB)
chumby:/mnt/usb# cat iwconfig.txt
rausb0 RT73 WLAN ESSID:"2WIRE729"
Mode:Managed Frequency=2.427 GHz Access Point: 00:1F:B3:05:F6:E9
Bit Rate=9 Mb/s
RTS thr:off Fragment thr:off
Encryption key: (a WEP key)
Link Quality=85/100 Signal level:-54 dBm Noise level:-79 dBm
Rx invalid nwid:0 Rx invalid crypt:0 Rx invalid frag:0
Tx excessive retries:0 Invalid misc:0 Missed beacon:0
chumby:/mnt/usb# cat iwlist.txt
rausb0 Peers/Access-Points in range:
00:1F:B3:05:F6:E9 : Quality:85/100 Signal level:-54 dBm Noise level:-79 dBm
00:22:3F:9A:12:4D : Quality:69/100 Signal level:-70 dBm Noise level:-79 dBm
00:22:A4:E4:03:F1 : Quality:93/100 Signal level:-46 dBm Noise level:-79 dBm
00:0C:41:66:71:49 : Quality:100/100 Signal level:-34 dBm Noise level:-79 dBm
chumby:/mnt/usb# cat network_status.txt
<network>
<interface if="rausb0" up="true" link="true" gateway="">
<stats rx_bytes="25614" rx_packets="330" rx_errs="0" rx_drop="0" rx_fifo="0" rx_frame="0" rx_compressed="0" rx_multicast="0" tx_bytes="2046" tx_packets="28" tx_errs="0" tx_drop="0" tx_fifo="0" tx_colls="0" tx_carrier="0" tx_compressed="0" wifi_link="85." wifi_level="202" wifi_noise="177" />
<error>failed to obtain IP address</error>
<error>chumby.com is unreachable</error>
</interface>
<configuration gateway="" ip="" nameserver1="" encryption="WEP" key="[Our WEP Key]" hwaddr="00:0C:41:66:71:49" nameserver2="" auth="WEPAUTO" netmask="" type="wlan" ssid="shyster2" allocation="dhcp" encoding="hex" />
</network>