Unfortunately to get the most out of Outlook, you need to be using Exchange (no surprise there) for mail otherwise it becomes a vanilla mail client. But you can get around somethings....
I have a full complement of aliases on my iCloud account and it seems that the only way to select a different outgoing email address is to manually edit it in Preferences Accounts > Email address
To replicate Mac Mail's aliases, set them up as individual accounts, primary and then secondaries (try SMTP only for those), at which point you'll be able to change the FROM field when creating an email.
Also there's no archiving.
Unless you're mail provider is handling archiving, then, as you have found, you're limited to PST exports.
Although arguably you can replicate something similar by using Outlook rules and creating a rule to move mail to an "Archive" folder after X many days.
Similarly, you can create a rule again to delete mail from X,Y,Z folder(s) after X many days.
None of this is anything to do with the rules.
Outlook rules are extremely powerful and it's one way to replicate
some server-side functionality that your mail service doesn't provide.
Even in the windows desktop client some rules only run in the client. If you close the client. Turn off the machine etc. Only a much smaller sub set of rules on the exchange server in the background.
Sure but it depends on what control of the Exchange server you have. But Exchange has a lot of built-in policies to handle basic tasks like archiving and mail retention etc.
I assume the Apple client might be similarly less featured. It's office VBA model is limited compared to the Windows version as well. Never used it on Apple though so I could be completely wrong.
It's a lot better since they've merge a lot of the codebase but as you rightly say, there is still some parity issues between the two platforms. Although i believe VBA and Macro's are now supported to some extent but it's not something i've ever had to use whilst in a Mac environment.
let me see if I can find the original link.