Based on historical data pertaining to the Krummhörn population (eighteenth and nineteenth centuries, Germany), we compared reproductive histories of mothers according to whether the maternal grandmother (MGM) or the paternal grandmother (PGM) or neither of them was resident in the parents’ parish at the time of the mother’s first birth. In contrast to effects of PGMs, we discovered conditional differences in the MGM’s effects between landless people and wealthier, commercial farmers. Our data indicate that the presence of the MGM only lowers the woman’s age at marriage (AAM) and her age at the birth of her first child (AFB) in the case of landless families. However, among commercial farmers, who can generally be characterized by a lower AAM and AFB, we found opposite tendencies for the MGM’s effect leading to a relatively small delay in AAM and AFB. Moreover, we also analyzed differences in the completed fertility (i.e., children ever born, CEB). Results indicate that landless families in general do have fewer CEB compared with commercial farmers except for those families in which the MGM has been present. Emphasizing that the adaptiveness of investment decisions should depend on the interaction of genetic, lineage-specific (intrinsic) and ecologically imposed (extrinsic) constraints, we conclude that kin strategies consequently address different fitness components under different conditions.