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Categories and Groups - Outlook 2013, Outlook.com, Win8 and WP8

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Looking for someone to clearly outline the Best Practices around using Categories in Outlook 2013 that relate for those of us with Outlook.com accounts.

I have over 400 contacts and before, used Outlook 2010 categories to sort them as Friends, Family, Hobbies, Religious, Work, Restaurants, School, Scouting, and many others. I get that they're all wiped clean now after migrating to Office Home 365 but before I recreate all the categories from scratch, I'd like to know how I could sync this "filing system" of mine with Outlook.com? Doesn't seem to be any way to separate contacts except for Favorites?

I've tried to keep it simple and don't merge any Facebook, LinkedIn, or other social network contacts.

Do the Outlook 2013 and Outlook.com teams work together? What's the synergy between the two?

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