Convert Outlook 2010 PST to mbox to maildir to Gmail
Officially this is easy. Configure Gmail IMAP on Outlook client and do drag-and-drop. Great unless you have 10GB of emails from over 15 years to transfer. Besides all of your emails will be to/from "undisclosed recipients" on Gmail. Finding some ancient email is already difficult, but stripping sender and recipient info makes it next to impossible.