I kinda hope they hold on to Pompey. The Jays will need a 4th OF anyway and no sense losing anyone with even a tiny bit of upside for nothing since we are rebuilding. But yeah, not being called up in Sept combined with his attitude issues in AAA probably spell the end for him. He'll be in Atlanta by November.
Other than that, I don't think there is a crunch. Even when the Jays start adding all the talent they need to add (Wall, Waguespack, Perez, Ramirez, etc), they still have enough s*** on the 40 man as is that they can jettison. Once they start adding FA's, then it will possibly be an issue.