MVC + IIS7 = CSS Issue
From Control Panel, go to Turn Windows features on or off, then check Static Content in sub-sub-sub node of IIS.
I hope the continuation of this thread conveys a willingness to make sure this problem doesn't drive anyone off the cliff. There's a lot of documentation in various forums about solving this issue on Vista but I couldn't find any likewise articles for 2K8. As indicated in this forum post I was able to fix the issue on a Vista machine. Alas, a like execution failed to resolve the matter on 2K8.
I had verified that the StaticFileHandler had been included in the web.config as suggested in this blog post at apijunkie.com. Still, no luck.
Clarifying no luck, here - My server-side functionality was perfect. All MVC routes work like a champ. Just all CSS and JS rendering failed. When browser pointed directly at CSS or JS files resulting page was an ASP.NET 404 and not the traditional 404 error page.
So I went into the IIS7 Manager and into the Handler Mappings dialog. I added a new handler that specified the System.Web.StaticFileHandler type and gave it an extension of *.CSS. Then I repeated that for *.JS, *.PNG, and *.GIF files. When I refreshed the site in the browser, everything rendered perectly. The screen shots below demonstrate this process.
The Handler Mappings Window:
(source: windows.net)
Adding a new Managed Handler
(source: windows.net)
This resolved the problem, and now I have a perfectly functioning MVC app hosted in W2K. Time for a Guinness.
The problem was in the way I created the application. According to the forum thread located here, I needed to select the "Classic .NET AppPool" to fix my problem. Gotta love progress!