Michael,
By disabling "Keep accept Encoding" on the HTTP profile for the VS, the issue has been resolved. Like mcaulifn, however, I would like to know what kind of impact this setting change might have on ActiveSync clients. In my current environment, our ActiveSync devices aren't hitting the F5 but at down the road, we will want them to. mcaulifn also raises a good point; if that setting is known to cause issues with OWA, why does it remain in the deployment guide? mcaulifn, depending on your configuration, the use of Nagle's Algorhithm can cause a delay in Outlook connecting; we disabled it here on our client profiles.