Personally, I think this coming off-season is a big one for Pritchard (assuming, of course, that he's not actually being fired). He's built a team with a lot of talent, but I think Aldridge's stagnation, and Fernandez's collapse, changes the upside expectations of this roster a bit.
When the hope was that Roy, Aldridge and Oden would all be All-Star-caliber talents, and Batum, Fernandez and Bayless were talented wildcards, this roster looked quite golden.
What I think we currently can say: Roy is in fact a perennial All-Star talent. Oden showed that he likely is one, too, if he can stay healthy. Batum has gone from wildcard to talented complementary player (with further upside). Bayless remains, IMO, a talented wildcard...his production this season jumped from last season and he's stepped up in the playoffs.
However, Aldridge doesn't look likely to become an All-Star talent. He's stagnated two seasons running, and it appears his prime is likely to be just a cut below All-Star level. Fernandez is starting to resemble an older Martell Webster minus the defense: inconsistent shot and without the ability to create plays.
It's possible that that, with full health and some more development from Oden, Batum and Bayless, this core will win a title. But it looks a lot dicier with Aldridge settling in as a complementary player rather than as a star.
Therefore, I think Pritchard probably needs to make a Big Move to get Portland out of "title contender if absolutely everything breaks right" status. He has a few tools...he can deal JPEC, Bayless and Aldridge for that boost. Batum is a possible chip, if the return is really big (because, at that point, Portland would be a three-man team long-term...so it better be a great third player). Chris Bosh is an obvious target. I'd target Amare Stoudemire, too, if I were Pritchard. I've always like Devin Harris. Any one of these guys is extremely unlikely, so I'm not going to argue exact scenarios for acquiring each...but I'm hoping that exploring all the options for these guys (and other impact players I haven't mentioned) will yield something that works.
Basically, I don't think Portland should sit still with this roster. I still like the upside of Oden, Batum and Bayless, but I wouldn't count purely on internal improvement. I think the team needs to make one aggressive move to improve the front end of the rotation at the expense of depth. A four-man core of Roy/Oden/Perennial 20-22 PER Player/Batum is definitely championship worthy. Even a core of Roy/Oden/Perennial 20-22 PER Player is probably sufficient, if they can just fill out the roster with guys who can do anything (shoot from range OR defend OR rebound, etc).
As a fan of Pritchard, I think this his remaining major task. I think he's done an amazing job to get the roster to within one big move of a serious multiple title contender. But now it's absolutely time for that one big move.