I’m experiencing exactly the same behaviour as JEL for items 1 and 2 (I haven’t tested #3), I just hadn’t got around to messaging here.
It’s kinda like someone wrote the code but FORGOT TO ACTUALLY USE THE ADD-IN using Outlook on a Mac. Which, based on how long we’ve waiting for the functionality is probably what I suspect has happened.
I also communicated directly to HubSpot a few months ago that I think HubSpot should have a proper menu bar app running on a Mac - just as DropBox, TeamViewer, Skype and all the other SaaS platforms I interact with already do. I’ve been forced to use Chrome to access my email tracking stats, and the Outlook add-in is not in the same league as the Windows system tray app I used to use.
Over to you, HubSpot…