The present paper deals with the practical problem of reducing statistical uncertainty in elastic settlement analysis of shallow foundations by relying on targeted field investigation with the aim of an optimal design. In a targeted field investigation, the optimal number and location of sampling points are known a priori. As samples are taken from the material field (i.e., the ground), which simultaneously is a stress field (stresses caused by the footing), the coexistence of these two fields allows for some points in the ground to better characterize the serviceability state of structure. These points are identified herein through an extensive parametric analysis of the factors controlling the magnitude of settlement; the number of different cases considered was 3318. This is done in an advanced probabilistic framework using the Random Finite Element Method (RFEM) properly considering sampling of soil property values. In this respect, the open source RSETL2D program, which combines elastic finite element analysis with the theory of random fields, has been modified as to include the function of sampling of soil property values from the generated random fields and return the failure probability of footing against excessive settlement. Two sampling strategies are examined: (a) sampling from a single point and (b) sampling a domain (the latter refers to e.g., continuous cone penetration test data). As is shown in this work, by adopting the proper sampling strategy (defined by the number and location of sampling points), the statistical error can be significantly reduced. The error is quantified by the difference in the probability of failure comparing different sampling scenarios. Finally, from the present analysis, it is inferred that the benefit from a targeted field investigation is much greater as compared to the benefit from the use of characteristic values in a limit state design framework.