Re: Mac questions
I don't remember off the top of my head if outlook can export the contact list. Even if not there's probably a tool that will give you a .vcf file that you can just open using the contacts app, which will import it. The contact list is actually a feature on the OS level, not a part of the Email program so any app can access it.
If you start typing in the to field, Mail will complete the address. If it gets it wrong you can actually use the up and down arrow keys to explore other options. Next to this you do have an "add from contacts" button that opens a simple window with a search box, and 2 trees, one with all of your groups and one with your contacts sorted alphabetically, so you can choose things that way as well.
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