Yes it is certainly possible. You can create the folders yourself in Outlook. Certain email applications require extra steps to subscribe to an IMAP subfolder, but if you're using Outlook on both computers there's really no extra steps to make the folders accessible.

As always, the first thing you'll want to do is to back up your current PST files. You'll then need to set up the IMAP connection. You can't change a POP connection to an IMAP connection, so you'll just have to create a new one. I generally recommend creating a new profile within Outlook so that you have the old POP profile intact, just in case.

Once you've set up your connection to the IMAP server, create your subfolders and then start importing your PST. Any data you place into a folder on your IMAP connection will sync back up to the server on the next Send/Receive. If you have a lot of data, you may want to go one folder at a time to avoid bogging down your connection.

Once you've setup and synced up your email on one computer, all you need to do is create the IMAP connection on the other computer. The other computer will automatically read the folders and sync with the email you have already uploaded.

You should double check your mailbox space quota with your ISP to make sure it's sufficient for the email you're going to receive, as all the email will remain on the server until you archive it off.

-SW