There are many sites out there dedicated to importing your email into gmail, this is not meant to be another. This little page is here to document the method that I used specifically to import sent mail into my gmail account with the correct date and have it show up in the sent mail section.
I used Mark Lyon's Gmail Loader on OS X (Mac specific instructions). Gmail loader just reads mbox files, parses them and sends them to you gmail account. When the mbox file is a sent mail folder, then it also sets the from address to be the gmail address you are sending to.
One catch is that the mail will be time stamped with the current time on google's servers rather than the time that the message was sent/received. A trick to get around this is to use a third gmail account. Use Gmail Loader to send all mail to a temporary gmail account, then setup your main account to pull mail from the temporary gmail account. When it pulls the mail it will correctly set the date and time.
This is where I ran into a problem. If I import sent mail to temp@gmail.com, it works fine in the context of temp@gmail.com. But as soon as it gets transferred to my real Gmail account it no longer is from me, but from temp@gmail.com. To get around this I simply edited the Gmail Loader python script. At the point where it sets the from field to be the destination gmail account (i.e. temp@gmail.com), I hardcoded it to be my real gmail account. For me this is at line 302:
fullmsg = re.sub(r'From: .*', 'From: my-real-email@gmail.com', self.msg.__str__( ) + '\x0a' + self.document, 1 )
server.sendmail(self.recipnt.get(), self.recipnt.get(), fullmsg)
else:
fullmsg = self.msg.__str__( ) + '\x0a' + self.document
server.sendmail(self.msg.getaddr('From')[1], self.recipnt.get(), fullmsg)
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