Both are beautiful bags and it sounds to me like your expectations may be too much for one bag. They are so different and I use them very differently. What is it about the Crosby you don't like? Teal is stunning, but not always the most versatile color. The Dakotah is gorgeous as well, but edgier. Sometimes I like edgy, and sometimes I like more structured and sophisticated.
Instead of looking specifically at the style of the bag, think about how you would use each of them and see what works in your closet. Also, look at other colors and styles and think about what might be duplicative.
I have the vermillion Borough and I desperately love currant red!! I thought about the Gramercy in red, but I don't want two red satchel bags.
I am not sure this helps at all, but I thought I would share my thoughts as I am struggling with a purchase decision.