Using classic Outlook for Windows in business environments
I'm running Outlook 365 on two W10 machines and haven't had a single issue, only my Gmail for android (which uses app password) has had the problem.
If yours is working and just giving annoying password prompts then I guess you can just hope it resolves, but I do know they've been phasing out standard passwords for a while now so at some point soon you'll want to move to modern auth with 2FA etc.
Looks like Outlook 2019 now supports modern auth by default, not sure if you installed it before that update if they updated you automatically or if you have to go update the registry. But if you upgrade your account to 2FA and remove/re-add it with modern auth, that should theoretically solve your issues.