How to add Outlook to "Share" popup menu in finder
I found a temporary work around.

In Automator services, I added a new service! 

And it works for me just fine, till someone comes up with a better solution.

See my screen capture for specific details how to (should be easy to follow since it is my  first time I used Automator) and I am a Dummy.



Important is to select your email service of your choice (gmail in my case) to send messages and attachments.

That will tell the OS X Mail client to use that service to send emails.

Save your Automator service file (give it a easy name you want to appear in the Finders right click popup window). Something like "Send file by email".

Now when I right click on a file in Finder it shows that service at the bottom of the popup window. Now just follow the instruction and see it work.