I’m not sure how this plays into this but I’ve asked my Rebbe regarding complimenting the girls on dates and such because I was concerned that it might be inappropriate/assur. His response was “do what’s normal and expected of you”. Regarding how many times to go out during the engagement period, he said every person is different and there isn’t a set rule. Do what feels right. Basically do whatever is normal and be sensitive to the girls needs because there is no one size fits all. If this was a clear cut assur I’m sure my Rebbe wouldn’t have told me that. This is a gray area which depends on the circumstances. I think you could apply this to much of the conversation above.
(My Rebbe is not from cc so dont make any assumptions)