@Dchiplin - in the ios reader plugin customization, you can enable debug logging. Only problem is, I am not that familiar with Calibre so I don't know where the log goes. Perhaps someone else can chip in here?
Alternatively, one of the changes I made during the port to Windows was to also write all debug logging to the standard Windows debug output. You need a viewer to see this, I suggest DebugView, which you can download or run directly from here:
http://technet.microsoft.com/en-gb/s.../bb896647.aspx.
Also make sure you are using the latest dlls from the first post, as I have updated them twice today. There was a fix to a bug that can prevent connections.