D'oh! My get-rich-quick scheme has been foiled!
On the (very) bright side, Stephen Foskett, a fellow pack rat, has figured out a way to upload your email archives into GMail that is going to save everyone a lot of time. No installing POP servers, converting to CSV files,
or losing your email timestamps-.
You basically just turn on IMAP in Outlook and in GMail, and then copy emails into GMail by dragging and dropping onto the appropriate GMail folder. Uh, pretty simple and elegant. Way to make us look dumb, Stephen!!
Why I never thought of this, or Louis never thought of it, I have no idea. I guess we were fixated on PST files and forgot about IMAP, since it is so new within GMail.
Update: Actually, when you copy email this way, GMail stupidly timestamps it with the time you copied it, instead of with the actual times in the email header, just as with SMTP delivery methods. So copying emails from 2002, they show up as new, sort as new, summary timestamp in list views is new. Only once you click through to the message can you see the actual date and time.
Hopefully GMail will fix this. Until then, POP3 seems to be the only way to get something into your GMail account and have it sort and summarize the timestamp property.
Update2: Based on the second comment from Stephen Foskett in this thread and some workarounds/fixes I read about in the GMail Google Group, I am hopeful I can get this working in the next few days. Jamming at work right now, though.