TragicMonkey
Poisoned Waffles
I thought one of the advantages of Active Directory was it served as a central repository of "truth" for the domain. But Outlook isn't not syncing? Are you using Exchange, or another email server that can't consult an LDAP database for authentication? I can see Teams having poor integration with AD, given that it's web-based. I don't know if Microsoft's 365 family integrates with AD at all.
I have no idea, I'm not a networking person. Networking stuff put me to sleep in class, and it still does. I suspect the problem is too many things trying to interact between remoting in and regular network stuff and Windows and the extra security junk and the other stuff. All I know is that I end up with my new password committed to muscle memory by the time I get it working everywhere it has to!