Yet another update.
After doing all this and getting it to work, if I pop out the objectives window from the default position on main monitor, then exit and fly again through world map it will crash. So I have to go back to flight training and set the window back to the default “unpoped” position for it to work again (as explained previously).
Oh well. At least I know more about the bug and can repro this easily (and have a better workaround).