I guess this issue and my other post (http://www.dotnetnuke.com/Resources/F...) are related based on the links provided in the other post

@Sebastian thanks for the help, I checked the EventLog table and it is also not showing any more information.

@William thanks for the help, here are the answers to your questions:

1. Yes this is a ASP.Net 4.0 site
2. IIS V6.0
3. I ran the upgrade on localhost while debugging, so in that environment the UserPortNumber is uncommented and set to true .  On our development server, it is commented out and uses Port 80. 
4. Yes, but only some
5. Yes, and they reappear when deleted (see post link at top of reply).  Interesting point, these automatic portal aliases for images only re-appear when browsing through my localhost while debugging.  When I hit this website on the develoment server (which shares the same database as my local version)  there are not any portal aliases created for images.
6. Hit the site through debugging locally without default.aspx, just the root url (http://localhost:5435/DNNclient, where DNNClient contains the DotNetNuke framework)
7. No

Bill, this works.

However, it leaves my unable to use extension-less page names and I cannot use Will's ActiveForum and ActiveSocial rewriter.

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This could be a clue for someone.. On my IIS 6.0 box every time I go to my root domain name and get the DNN error I have this in my Event Log on the Server:

Exception information: 
    Exception type: HttpException 
    Exception message: Server cannot append header after HTTP headers have been sent.
   at System.Web.Hosting.ISAPIWorkerRequest.SendUnknownResponseHeader(String name, String value)
   at System.Web.HttpResponse.WriteHeaders()
   at System.Web.HttpResponse.Flush(Boolean finalFlush)
   at System.Web.HttpRuntime.FinishRequest(HttpWorkerRequest wr, HttpContext context, Exception e)