Reading many comments here, it's frightening how far out of touch Microsoft / Outlook designers and developers have become on recent years. They're damaging a great product.
Outlook has always been a very complex program because it needs to cater for innumerable case scenarios for working people, across all sorts of industries and institutions. There can be no "one size fits" all in order to meet their needs.
"Dumbing down" Outlook for the "newbies" and non-technical, non-power users is simply damaging everyone else. What you really need are different versions of Outlook, and even Office, a Light Version, in fact you have it already with the web vs client versions. Changing the client version to be like the web version is a major error in strategy, the customers are different, with completely different needs.
Stop changing things for the worse simply for the sake of change, you're alienating tens of millions of your customers worldwide.