Ok, whoever let this out of the door at Microsoft without resolving it is fired. Apparently, as described in this article: http://blog.aaronmarks.com/?p=65 there is a problem with running exchange and outlook anywhere on windows server 2008 such that if IPv6 is enabled in any form, you cannot connect. The nitty-gritty details come down to the server not listening on port 6004 for some reason when IPv6 is enabled... you can try it yourself by running "Telnet localhost 6004" in the command propmpt... no response.
Long story short, enabling the registry entry detailed in that article, unchecking ipv6 on the adapter, and removing the ::1 localhost entry from the hosts file then rebooting cleared the issue right up!
(For those wondering, the issue I was having was that outlook web access was working fine, and outlook was connecting just fine inside the network, but when i tried to use outlook anywhere with outlook 2007 outside the network I would persistently get an error indicating that outlook had to be online in order to connect.)