If the web version and the desktop version of Outlook continue to be so different, you need to make them different products. You also need to decide if your competition is gmail and yahoo on the web, or is your competition your own proclivity to try and grab all the cookies from the cookie jar and then not be able to pull your hand out of the jar while holding all those cookies. Similarly, if you can't find some way to provide Enterprise tools for an affordable price to small businesses of 1 to 5 people, then you can't really expect them to happy about recommending your products to their small business customers.
Either your goal is to be the monopoly and the only company viable for every user to choose, or you need to become able to resist crushing every other company in the market with your world class law department. It appears your success is more due to having the largest and most capable group of lawyers on earth, rather than having the largest and most capable group of engineers and developers.