This is a late reply I know but...
The webrequest timeout appears to be broken in the Netduino. If the webrequest target device is not available the request will simply wait forever and hang.
I got around the problem by wrapping the webrequest in a ping request. If the ping succeeds the webrequest is executed. If the ping fails the request is bypassed.
I used this version of Ping and it appears to work well: