Trying to find the search button, depending on what you have open it is hidden completely.

That it will automatically try to disable com add-ons even if you tell it not to or create a group policy that tells it not to disable certain add-ons. Still on some machines they will disable. Disabling and re-enabling them from the list often won't fix the issue as you have to first re-enable them in another menu. If neither work then you have to completely re-install the add-on.

Its popularity.

Outlook like many of Microsoft's products could really stand to be just eol'd and then replaced by a better product

When I click in the search-box in the titlebar, Outlook freezes for about 5 seconds.

You can't cut and paste an appointment.

I tried making a template the other day. I was successful, but it's multiple clicks whenever I want to use it. There's no way to customize the ribbon and add a button to use my new template.

At work we constantly have issues requiring the need to recreate the Ms outlook profile. We made a script for deleting and adding back the ocp or whatever it's called