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Android's Contacts displays the contacts in both your Google account(s) and your Microsoft account(s) including Skype. I generally only keep contacts in my Outlook.com account (aka, Windows Live, Hotmail) of those with whom I correspond using my Outlook.com account.  Outlook.com includes Skype contacts, which are sometimes separate from the contacts I create in Outlook.com's People.  However, Android combines Gmail's and Outlook.com's contacts into a single contact. Updating Gmail's contacts on your PC appears almost immediately on your phone and vice versa.  Updating your Outlook.com People contacts usually takes several minutes and the phone's contacts sometimes show old information as well as revised information.  Outlook updates probably take longer to propagate through the system and you may need to reset your phone's Outlook account.

There is also an Android Outlook app and it too combines Gmail contacts with Outlook.com contacts.  It took shows old information as well as revised information while changes propagate through the system.  Sometimes manually resyncing/resetting the Outlook account or refreshing the Outlook.com contacts is necessary to speed up the process.

I find that Gmail's contacts work better than Outlook's.  Gmail allows custom names so that you can label one phone number as "home" and another as "cottage".  Outlook.com is less flexible because the labels are not customizable and have a limited number of permissible names.  If you wanted to include a cottage phone number for example, it would appear as "home 2"

Outlook.com and Skype contacts are separate.  If you add someone as a Skype contact, they will appear in your Outlook.com contact list.  It is better to add that Skype contact with "Add to contacts" rather than starting a new editable Outlook.com contact for that person.  This will appear as linked contacts and you can delete the Outline Online contact if you want to start over.  You can potentially use the "Clean up contacts" function to merge contacts but this can produce unwanted results if two separate people share the same name.  It's safer to delete the non-Skype contact for that person and then "Add to contacts" that Skype contact.

Speaking of contacts, complete your own Google+ and Outlook account profiles so that your friends (check your privacy settings) more easily be able to find you.