Justin,In your number one question don't use localhost spell out your machines name.Number two depends on the version of IIS you are using is this directly on the server that you are developing? Is it Server 2008? or are you on your desktop and using XP?
Justin, Do you have IIS installed on this machine? I can take my development machine and disconnect it from the network and have no internet access at all and as long as my FlexViewer is pointing to mapservices that are on my laptops ArcGIS Server than everything is fine.
Have you tried using a tool like HttpFox, Firebug, Charles etc. to see what HTTP requests are being made and which are failing?
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