You have said two things that really have stuck with me and I am not sure why exactly but they really stand out to me.
Y'day you said something along the lines of your W having a bright future w/her career but not as bright as yours but still pretty good. Above you said her self esteem is not where it should be but not "real bad".
I am not sure judgemental is the word I would use but you sound like you have a "bar" in mind for your W that only you know about.