As has been pointed out, JA does not let us into CW's head until late in the day, and it is jarring. As a male reader, perhaps I can imagine myself in his shoes, and be an advocate for him.

He dwells on her "timidity." Yes, he wanted her to stand up to her bully-father, and her snobby friend, LR. But, underneath, perhaps he does not think she could love him much if "persuasion" can have such an effect. Perhaps, he thinks, Anne does not realize it herself. Now, we, the reader, KNOW that is not the case. But CW does not.

So, for summary (CW's mental outlook):

-- family bullies her
-- money means alot to her
-- fancies she is in love, but really isn't

In other words, according to CW, eight years ago and in the present, she is not BOLD enough to know her own mind and go her own way.

Personally, I like the Persuasion Archive material (the present discussion has also been very illuminating :)). One reader believes that CW exalts her, puts her on a pedestal. I'm swayed by that argument. If CW exalts her, he lives always in insecurity, thinking that her feelings could not possibly so strong as his. A destructive mind set, I grant you. CW is always on the lookout for evidence that she is indifferent, or is in love with love.