Yeah... this is of course not at all unique to Apple -- but sadly, that would be a typical "script reader's" response, in any 1st-tier tech support shop. The first entry on their script is always some variant of "Have you tried turning it off and on again?" but after that, it rarely takes long for them to reach "Ensure the customer is running the latest version...". I've found that some will even refuse to provide further support, based solely upon a customer refusing to choke down a major software update.
It seems to me that your most likely path to successfully logging into an Outlook.com account would be to use the Microsoft Outlook mail client instead of Apple's Mail client. Alternatively, you could try digging through Microsoft's own support forums for more information; I'd expect that to be a 50/50 shot, but still worth exploring if you really just prefer Mail.