. . .does he intend, really, that Anne should hear these remarks as covert criticism of herself, and should be hurt by them? Does he have any reason to know that she's paying that much attention to him, or that she cares enough after all this time to worry about what he thinks of her? I see these remarks as part of his conversation with himself, which sometimes spills over in public (rather like the "altered beyond knowledge" remark).

And petty? I don't know -- is it petty to feel (still) angry and hurt over the most devastating rejection of your life? He's a man who feels deeply and passionately. Yes, he should try to see it from her POV -- hmm, perhaps this will be his journey in the novel: but no spoilers here -- but seeing it from her (and Lady Russell's) POV might require him to interrogate his unshakeable confidence in his own abilities and prospects, and that unshakeable confidence is essential to him. Without it, he's unlikely to rise in a world in which success is largely based on inherited rank and wealth.