1) You'd need a constant connection to your calendar wherever it is stored in order for the regular customer to have that option. And then you start running into all sorts of problems
2) KB-01451 (Livelink - Redirection
) will walk you through enabling advanced logging and then you can see which record is causing the problem. When you get to Task 5, open up the tif.log file and scroll to the very bottom. In quotation marks, the last line will have the subject of the record that is causing the crash. Look for that subject line in your Outlook Calendar.