Hi Lee, thanks for posting here in Microsoft community, it sounds like the update may have corrupted your Outlook profile or removed legacy support for certain account types.
Since Classic Outlook can't log in and New Outlook restricts account access, I suggest try creating a new Outlook profile via Control Panel > Mail > Show Profiles and re-add your accounts.
If that fails, consider rolling back the latest Windows update or checking if Outlook profile registry keys were affected.
You might also try Outlook Web Access (OWA) temporarily to retrieve your emails and calendar.
Also, to isolate the issue, are your affected accounts IMAP/POP, Exchange, or Microsoft 365 and were they added manually or auto configured before the update?
I hope this helps you out, let me know
Chard