We're always seeing customers call in developer support on problems related to their addins often being intermittently soft-disabled. 

If you're running Outlook 2007, here is one way to log whats happening inside outlook to aid in your troubleshooting.

You can enable Outlook logging in Outlook 2007 by:
-              Go to File… Options…
-              Select Other tab
-              Click Advanced Options
-              Ensure “Enable logging (troubleshooting)” is ticked
-              Ok out

Log files are created as .etl files and stored in %userprofile%\Local Settings\Temp.  A new log file is created each time Outlook starts.  The log file created may or may not help with isolating the issue with the add-in but might give you a better idea of where to look.