Is there any reason why you cant use cloud sync? I'd think it would best to use cloud sync rather than USB sync for multiple computers. The computers would obviously have internet, so install Go Contacts sync and GCal sync on all computers where you want to sync Outlook. They will constantly update each other via Cloud on the Google Servers (Calendar and Contacts). Any changes in one computer would be reflected in Google Calendar and Google Contacts and Outlook on other synced computers. For your phone, if you dont have a data plan to use mobile internet and have packet data off, just turn on Google Sync. Everytime you connect to WiFi, your phone's contacts will be updated by GOogle servers. If you also change anything on your phone, when you sync to Google, your Outlook will also be automatically updated once they sync again (depending on the schedule you set for syncing on Go Contacts and GCal.