Hi Tony Murnion,
for the first issue, I am wondering if you have Outlook 2007 or Outlook 2010? For SL 2011 you will need Outlok 2010 with the VSTO add-in installed.
To install the VSTO add-in please go to the following folder:
C:\Program Files (x86)\Microsoft Dynamics\SL\Applications\OutlookAddin
once there please run the VSTO installer
I am also wondering, when you start the application server, do you see any errors?
for issue #2,
I am wondering if the user is having permission issues. Please download the process monitor from the URL below. Run the process monitor on the users workstation while the user recreates the crash. Once the user sees the crash, stop the trace and search for a Access Denied result. If any are found, please provide proper permissions.
925032 How to use Process Monitor to troubleshoot system errors that are caused by file access problems in Microsoft Dynamics SL