I totally enjoy discussing the these things, helps give a broader picture of what happened, and what might happen. jPk has his own plans, but sometime people pick up cool angles that weren't intended, and he threads them in. I remember someone discussing that John's habit of being casual when chosing clothes was a reflection of Ell'a lack of pretentiousness. I liked that reading of his character a lot.
About the dad - we don't know what role the dad has, what he's done other than being a bad parent. He's obviously done something that's severely affected his ex wife and Charlotte. Consider that Claire was also a bad mom. Why isn't she still with John's dad? What caused the family rift? I don't think it was just Ella at this point, I can't imagine Claire leaving her husband over John's marriage, and that had nothing to do with Charlotte in any case. So that's a mystery yet to be uncovered. The way he's described as never giving anyone an advantage, and never letting a cent out of his grasp without profiting suggests he probably DOES mind the 10 million. But we'll see.
About Charlotte - if someone gets cold feet over a multi-million dollar deal, they'll walk in real life. Why would she through away the money just to hide the real deal? If John failed there, well the story would be shorter I guess. So I don't think Charlotte's goal with the meeting was to rubber stamp anything, or just see what she could trigger John about. I think if she got the wrong answer, the deal would be off. Just like John and Ben could've been offended about her tactics to the point of saying the deal is unmanageable.
I would say that she believed John would pass her 'test', but it was still a test and she did mean it. I don't see her words as contradicting anything she said on the bridge. She wants John to be a go getter, rather than flat on the pavement. Different circumstances and paradigms, different methods, carrot and stick, even if on the bridge she was still slightly aggressive with her kindness.
Having empathy and being ruthless are not mutually exclusive in a way. She prioritised her own goals at the meeting, which is natural, but she used personal, private insight as leverage at a business meeting. She is ruthless. She uses what advances her goals. Most people are kind when they can afford to be, not everyone is kind when it costs them their goals. Charlotte is clearly doing good through the charity, and her intentions seem pretty good. That doesn't excuse her methods, even if she gets the results. We can achieve our goals through wrong means: that's the problem of ethics and there's a lot of grey in this story.
About Lisa, sure she's Charlotte's preference to run the business, but she'll allow Lisa to do something else with her life if it means that much to her. She is better than Paul in that regard - she'll let Lisa do something for herself rather than for the family prestige. But, the business can't just close up shop because Lisa wants to do something different. So what would Chalotte do, other than have a second option? And regarding business and the way she also needles Lisa at times, she probably thinks the competition is healthy, and will keep Lisa engaged with the business. Carrot and stick vibes again.
I do believe Charlotte is the kind of person to follow through: if she doesn't see a good outcome, she'll make one.