Microsoft Account/s and Outlook 2013

Please advise on this scenario:

1. John's email is hosted on a Smarter Mail Server john@hiscompany.com
2. John buys a new Windows 8.1 laptop with Office 365 installed and signs into his Microsoft account using his email addressjohn@hiscompany.com
3. He gets an Outlook.com account john@hiscompany.com
4. He sets up Outlook to connect to his Smarter Mail server via IMAP
5. He adds his old Outlook 2010 PST data file archives to Outlook 2013
6. John's Windows Phone was set up by the phone shop last year with a different Microsoft accountjohn@live.com where all his contacts are stored
7. He adds an Exchange Active Sync account to Outlook 2013 to get his contacts fromjohn@live.com

This is causing all sorts of problems. OST file errors. Incompatibility with Outlook 2010 PST files. Non-syncing of contacts etc.

How can John get all his mail, contacts and apps into one account across all devices - preferably his main Microsoft accountjohn@hiscompany.com

He does not want emails labelled "Sent on behalf of"