Yes, it's easy to do both, get the extension and then the re-entry permit the same day using the appointment system. This is at CW. Good rule of thumb is to make the re-entry appointment about an hour fifteen minutes after the extension appointnent. (Re-entry appointments are offered 15 minutes apart from each other.)
Even if you get to the re-entry booth later than your appointed time---which I did one year when it took 50 minutes (a record!) for my passport to be returned to me at the extension section--with my appointnent booking in hand the re-entry staff just waved me in.