Multi-agent-based modelling and simulation provides an adequate environment to study the real world. This paper presents the use of a multi-agent research and simulation (MARS) framework and model design based on the overview, design concepts, design (ODD) protocol to model and simulate small-scale management strategies that are important for increased milk yield per cow. In reality, strategies for farm management at a small-scale level are purely based on heuristics that cost farmers and lead to inadequate milk yields. A differential assessment of the farming strategies was conducted to yield a data-driven approach for selection of the best strategies, which in turn will optimize investments and increase milk yield. The agent-based modelling and simulation revealed that, the studied strategies based on income, farm, and farmer-based characteristics influenced an increase of up to 7.72 L of milk above the average (12.7 ± 4.89). Generally, there was an increase in milk yield based on the identified evolvement strategies; from a baseline data average milk yield of 12.7 ± 4.89 to simulated milk yield average of 17.57 ± 0.72. Evaluating the agent-based models in real-world scenarios will strengthen the assurance that the identified strategies can move small-scale dairy farmers from low to higher milk producers.