I am contemplating upgrading Office Home & Business 2016 to an Office 365 subscription. Can the migration of Outlook be performed easily and seamlessly? I need to ensure that mail accounts, message rules, favorite folders, contacts, PST files etc can all be restored easily without complex re-configuring from scratch. What does the migration process involve?

Yes you can do this migration easily by using any of the migration tools like Gs Richcopy 360 and ShareGate ,both are GUI , fast and easy to use