Pintsize in a more human like body would be troublesome... both for him and everyone around him. Thanks to robot racism, anthro PCs with bodies like his or Winslows are both given more leeway on behavior and treated more like things than people. Where as ones with more human chassis like Momo and May are pretty much treated more like human. Treatment varies of course, but there is no way Pintsize would get away with half what he does now if he had a human-like chassis. But then again, he always wouldn't be casually thrown into walls, disassembled or have his head punched so hard it dents by people just meeting him either...
Disclaimer: I'm thinking aloud here, so I'm going to ask forgiveness in advance for any toes I may inadvertently step on (and am going to try hard not to step on any).
Thought one:
I don't know that Pintsize getting a more humanoid body is necessarily a bad thing. The first thing that comes to mind is Pinocchio; you've got a puppet who wants to be a real boy, but in between those two points, he's a liar and a bit of a fuckup, right? Might a similar dynamic be at play here?
Thought two:
I'd posit that Claire's trans* status wasn't Jeph's first foray into trans* issues in particular, or gender issues more generally. Might the fluid nature of AI identity, in all its facets, have been a test run for what came later with Claire?
Thought three:
In the same way that a trans* individual might seek to have their body conform to what they know themselves to be psychologically/sexually/socially (though this process has no single way of playing out, and there's a wide spectrum of gender identity and expression), might an AI not go through a similar process?
Thought four:
If an individual -- human or AI -- feels they're in the "wrong" body (that is to say, one that doesn't match what they feel to be their true self) or is otherwise denied full self-expression, wouldn't it stand to reason that some of their conduct would seem puzzling, if not downright inappropriate, to someone who doesn't understand where they are in their lives?
Thought five:
In the same way that a person whose presentation is more in line with who they know themselves to be would be presumed to be healthier and happier, might an AI given the chance to express themselves as they truly are also be more fully self-realized and self-actualized?
Tying all this stuff together: Pintsize has generally been played for comic relief, but has also shown a fair amount of insight from time to time; in that sense, he's filled the role of the Jester, who gets away with speaking the truth because he's putting it in a way that's funny.* But in contrast to May and Momo, nobody's really A: given any serious thought to, or asked about, his inner life or well-being, or B: given him the chance to be or become more than a punchline. Might it be possible, then, that if given a more sophisticated chassis, he would, in effect, "grow into it"? That isn't to say there wouldn't be some speed bumps -- if you're a Star Trek: TNG fan, you remember the learning curve that came with Data getting an emotion chip, for instance -- but it could be an opportunity to explore a totally different dimension to the AI experience, and make Pintsize more of a character and less of a wiseass prop. Given the sensitivity with which Jeph's handled Claire's trans-ness up to this point, Pintsize's "transition," and the growth it could bring with it, could be an interesting arc to watch.
*Of course, there's the other times, too, where he's just being an asshole