...because CW was a man of confidence and great expectations. He knew from 8 years before that he was able to attain the position and wealth if he'd wanted.

I'm not sure I agree that it's out of "anger and self-reproach at losing Anne" that had motivated CW's career advancement. I believe that CW had meant to advance regardless of anyone's opinion. "His genius and ardour had seemed to foresee and to command his prosperous path."

Only problem was that he was taking his time and frankly, enjoying life while there was still daylight. That was perhaps an overconfidence in his own abilities or a lack of oversight on his part that had caused an outward misconception of his character. Particularly in the eyes of a very opinionated LR. "Lady Russell had little taste for wit, and of any thing approaching to imprudence a horror." I would add that in addition to not having a taste for wit, LR also didn't know what it means to seize the day :-)

What CW had expected Anne to have done was to trust his judgment. Instead, Anne had trusted LR's. When she did that, CW considered it a loss for both him and Anne, but his life had to go on, and he did go on to live it the way he had planned all along. "He had, very soon after their engagement ceased, got employ: and all that he had told her would follow had taken place."

I cannot find any evidence in Anne's recollections in Chapter 4 that CW had possibly regretted not pursuing his fortune sooner, something that would have encouraged her not to view him as the loser in LR's eyes :-)