My take on all this is that while I don't want to tell you how to write your software, but handling all exceptions gracefully and never letting the IDE get into a state where it has to be restarted, or crashes on a catchable situation would be a good thing.
Nearly all issues I saw were related to doing things that could have a clean solution. If it loses connection to the device during debugging, don't get stuck forever, give the user the option to end the debugging session.
Cant open a file at startup, check for a null file handle before using it and start the IDE without opening a file with an error message. But I am sure you guys already know all this stuff!!!