Hi I'm new, but I figured I might as well jump in now; Do you think it's possible that they could turn it towards Pluto?
It is possible, but not likely. Jupiter was deemed worth the risk because of it's large size, moons, and the fact that it is a fair amount closer from Mars than from Earth, so we could get a decent picture out of it. Also, it helped to do characterization of the camera, because of it's well-known colors in various wavelengths. Pluto is small, very far away, and all in all, it'd only be a few pixels across, if that. It hasn't been as well characterized, and there isn't an advantage to looking at it from Mars, it just doesn't do anything different.
As an aside, Jason says now he's more interested in HiRISE because it's taken a photo of a "worthy" planet.