Systems and methods for real-time, artificial intelligence control of an agricultural work vehicle and/or implement based on observed outcomes are provided. In particular, example aspects of the present subject matter are directed to systems and method that sense field conditions (also known as field “finish”) both before and after adjustable ground-engaging tools encounter the soil and that update a site-specific control model that provides control settings based on the observed anterior and posterior conditions. Thus, a control system can obtain sensor data descriptive of upcoming field conditions and can perform predictive adjustment and control of tools based the upcoming field conditions. The system can then use additional sensors to observe the outcome of the employed control settings. Based on a comparison of the observed outcome to a target outcome, the system can adjust for the next encounter of similar field conditions.