I feel like Jane Bennet saying this, but I really don't see Henry assessing Catherine as a potential life partner by design. I think it all is happening naturally- the initial flirtation, Catherine's developing attraction and Henry's perception of it- all seem to be flowing naturally. Her finding him irrestible makes him reciprocate. He wants to get to know her more because he is interested in her, and also takes to gently mentoring her (echoes of Mr.Knightley, perhaps?). However, I don't see him trying to determine if Catherine is upto his ideals as a potential life partner in a business-like manner.