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I had Outlook 2010 and upgraded to Office 365, I didn't lose any emails. Everything migrated over. Not sure about multiple machines, I installed on two and all emails were there after the installation.
Sorry, there was a problem. Please try again later.Office 365 allows you to transfer your Outlook files. To learn about the transfer process, follow this link: https://support.office.com/en-us/article/Find-and-transfer-Outlook-data-files-from-one-computer-to-another-0996ece3-57c6-49bc-977b-0d1892e2aacc
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