andrewshelor

Agree with some of the responses. It depends on what you want to do with 'The Cloud'. My recommendation would be to write down what you want, then look at Office 365 and see if one of your needs lands in the Office 365 bucket of services. My guess is that you would surely utilize Exchange Online and SharePoint Online piece of O365. If you can get your current user's email exported to individual .pst files, migration (email) to Office 365 is very manageable.

Setup additional user called 'Share' and share out that users Contacts, Calendar, or Inbox. Having said that, if you are wanting to be able to setup a Contacts list and email to that list from Outlook (using To:), then you'll need to setup a Contacts list in SharePoint and connect to it from Outlook. The reason for this setup is that you cannot setup another user's Shared Contacts to be accessible from the "To:" command in Outlook. Wish that was possible but not yet. Another reason I had to go this route was due to a messy export/import from a previous Public Contacts list to a SharePoint Contacts list - the migration does not match up column to column and can be a nightmare. Yet if you export/import from Public Contacts list to Exchange Online 'Share' user Contacts list, then you'll not have any issues.