Cannot enable Messages on iCloud 10.13.5
iMac, macOS High Sierra (10.13.5)
Yes 2FA is needed,
Before you begin
Two Factor Authorization must be enabled on all devices before you get the checkbox to enable Messages in iCloud: How to Enable Messages in iCloud on Mac
Messages/Preferences/Accounts:
Try in Messages > Preferences... > Accounts
Cannot enable Messages on iCloud 10.13.5