I understand your concern but I am afraid I may not be able to offer much more than the Apple people you describe. It has been my experience that trying to fit anything Microsoft into Apple's universe is swimming against the tide. It's not as if I have not tried, but I don't like beating my head against a wall.
Microsoft's Office applications are very good in their own right, but the two company's philosophies have done nothing but diverge for many years now. That is the reason for recommending you do not attempt to marry their two organizational hierarchies. There are Microsoft people who cannot tolerate OS X, just as there are Apple people who cannot tolerate Windows. In case it's not abundantly clear, I'm in the latter camp. OS X just fits well with what I do, while Windows irritates me. It gets in my face and interferes with my work.
(There are also many people equally adept at using both systems, but I think even they would not seek to make a Mac work like Windows, or the other way around.)
Mail's appearance is deceptively simple but its customization is robust. You can create any number of folders and create simple rules for organizing your emails. You can label emails with colors or flags, and searching is easy. You can even search for deleted emails with Time Machine. I don't like keeping emails around so my needs are modest, but Mrs. Galt has fifteen thousand emails and somehow she copes with them just fine.
Outlook also has a calendar function (so I hear) but OS X's Calendar does everything I need. You can set up reminders, email lists, and automatic notifications. All the Mac apps are designed to integrate with one another, and with your iOS devices if you have them.
What I'm trying to say is that you will not become a Mac expert until you go cold turkey and abandon the Windows way of doing things - whatever that is. Using the aforementioned programs to cope with Office documents, I have been completely Microsoft-free for nearly two years, and life is better.
If you are fortunate enough to live near an Apple Store you should avail yourself of their periodic Workshops. They are completely free and you can pick their brains about what you want to do:
http://concierge.apple.com/reservation/us/en/workshop/
I have learned a lot about the Mac by attending these.