The structure of farms is associated with family characteristics and to sale strategy, for a given expectation of income generation and risk exposure. To understand this association, seven cases of settled families were studied in a land reform settlement in Araraquara-SP, Brazil, a region dominated by sugarcane and citrus plantations. The indicators were total aggregated value, the aggregated value per worker, family structure and dynamics and farm-work organization. The cases comprised two farms integrated with agroindustry (sugarcane and chicken, milk and chicken), three vegetable producers (selling in wholesale, semi-wholesale and farmers’ market), a family that produced exclusively for household consumption and a family without economic production. Families associated with agroindustry had the highest aggregated values, but had to make greater investments, which increased risk exposure. The world financial crisis of 2008 broke the agroindustries and both integrated properties. Vegetable producers had lower aggregated values than farms integrated with agroindustry, but their investments needs were accordingly lower. The choice for vegetable sale route was associated with family composition and with technologic and market knowledge present in the family.