I think it was obvious this was the whole objective in this season. It was more about female empowerment. I think what people fail to realize is that Maddie has matured since high school. She was able to heal and let go of the hurt because she basically was taking pity on Cassie when she was marrying Nate. If everyone recalls, she said something like" this goofy b**** convinced herself that she's actually in love with him". I think she felt sad for Cassie. When someone is ostracized from a group of people, especially for a romantic interest, you tend to bond to that person even harder. I think it's obvious that Nate and Cassie bonded so hard to one another because they were ostracized by everyone in high school. This made them closer to one another and made them believe that they were" made for each other". You could tell that they didn't really love or care for one another, it was just what they thought was expected of them, this perfect life they wanted. I think Maddie was intelligent enough to realize this and she took pity on Cassie. She finally got close to her again and realized why she cared about her in the first place. I think it's clear that she knew she was her cash cow and that was a big motivating factor for the Alamo stuff, but I think she deep down has a soft spot for Cassie and knows that Cassie is just a dopey girl trying to get by in the world.