Well, I am a glutton for punishment and I just couldn't let something so silly ride and after thinkning about it the re-image would take just about forever since I have a lot of data that would need to be moved... blah blah blah, etc etc etc.

So after poking around, I found that there is an option in Visual Studio that creates precisely this behavior ("reuse current document window if saved") under Tools->Options->General->Documents, but this is noticeably absent SSMS 2008 (though it exists in 2012). I figure if I can find that registry key and add it to the SSMS configuration, it should work, but after playing around I could not find what registry key this alters. I will do some digging and report back what I find.