As well as restarting with add-ons disabled, you might be interested in trying the new Beta. We've made some improvements there in general, i'm not sure about your exact Outlook issue:
If you can still replicate the issues with 2020.2 beta 2 and with add-ons disabled, if you could send us a log, at debug level, that would really help narrow down what is happening:
First of all, your NVDA key is either INSERT or CAPS LOCK, depending on how you have NVDA setup. So, to set your log level:
1) Press NVDA+control+g to open the general settings
2) Press TAB until the focus is on ""Log level""
3) Press DOWN ARROW to get to ""Debug""
4) Press ENTER to close settings
5) Press NVDA+control+c to save settings.
To restart NVDA with add-ons disabled:
1) Press NVDA+Q
2) Down arrow to ""Restart with add-ons disabled""
3) Press ENTER
Next, recreate the issue - do whatever causes problems.
To get NVDA's log after that, there are several ways:
If NVDA is still running and usable:
1) Press NVDA+F1 to open the log viewer
2) Press CONTROL+A to select all.
3) Press CONTROL+C to copy.
4) Open your email and start a message to info@...
, type a little about what you have done and what has happened in the body of the message, then leave a space and:
5) Press CONTROL+V to paste the copied log.
Instead of using the log viewer, or if NVDA has stopped and you needed to restart it or the computer:
1) Press WINDOWS+R to open Windows' Run dialog
2) Type %temp% and press ENTER (that's the percent sign, the letter t e m p and another percent sign). Windows Explorer should open to the temporary folder.
3) Press TAB to move to the file list
4) Press N and move down to find up to three files: nvda.log (the log file for the current or most recent NVDA session), nvda-old.og (the log from the previous session) and nvda-crash.dmp (a crash dump with more information created if NVDA itself crashes).
5) Depending on what email program you use, the steps will be different, but attach as many of those three files to an email to info@...
as will be useful, and again in the body of the message describe a bit about what has happened."