Rudy is an excellent ballhandler and passer, and he's very good in the open court. Obviously, he's a great 3 point shooter and finisher at the rim off a lob pass. I think his weakness is his half court game. Aside from spotting up for three and freeing himself up for the occasional alley oop, there isn't much to it. He doesn't have a good first step and is rarely able to get past his man off the dribble at the NBA level, though this could partially be the result of his injury. When he needs to go one-on-one at the end of the shot clock, he usually jacks up a contested three or takes some circus shot (ie the 15 foot turn-around fade-away off the dribble). Since Trevor Ariza undercut him, he's been shying away from contact more often. And that runner is garbage. Both of said shots are best reserved for a pickup game when the score is about 3 to 3. They're the kind of looks one should consider apologizing to his teammates for taking when they brick, which will happen more often than not. Why does he never seem to take a pull-up 15 footer or some other high percentage mid-range shot when he does get a little separation?
One of his strengths, and one that I think he should develop further, is his ability to move without the ball. Players like Rip Hamilton can hurt you from a lot of spots on the floor and tire out their defenders. While Rudy isn't as quick or well-conditioned as Hamilton was in his prime, he can certainly expend a comparable amount of energy in limited minutes.
One can argue that he isn't able to do this enough because of Nate's system or that is an issue of personnel, but I haven't seen evidence that Rudy has the kind of mid-range game that pays Rip Hamilton's bills in his repertoire. If he did, Rudy could make a legitimate case for being a starter on a decent NBA team when he is shipped out of Portland.