Using Outlook for Android in business environments for email and scheduling
In my case, the first problem that appeared was similar to your #2.
I also have the #2 issue since the October 9. I created separate email box on my mail server for testing purposes to prevent compromising my email box, if the Outlook used insecure connection on port 143 instead of 993 when no explicit port is entered in the IMAP account setup.
My experience is that there was no difference regarding the issue #2 having the port 993 specified or not. It had stopped working after a while in both cases. But I have had no issues with setting up the account nor a need to re-enter the password later. I always got the "Updating" message after a while and the account was over.
Th issues with setting up the IMAP account may be related to the way you deleted the old one. Outlook asks if you want to remove it from the device only or from all mobile devices. My experience is, if you choose the first option there is problem to setup the same account again.