I have an issue where the MonoDevelop debugger refuses to connect to the simulator. MonoDevelop pops a box saying \"Waiting for debugger to connect on 127.0.0.1:10000...\" b
It could also depend from content files (files with Build Action = Content) added inside some particular directories: e.g. you cannot create a directory called 'Resources' and put a content file inside, MonoDevelop hangs saying "Waiting for debugger to connect...." instead of raising a meaningful error.
See also this thread: http://forums.monotouch.net/yaf_postst361_Bug-or-Misunderstanding-Resource-Content--Black-Simulator-Screen.aspx