This thesis unites three papers discussing new strategies for matched pair designs using observational data, developed to balance the demands of various disparate design goals. The first chapter introduces a new matching algorithm for large-scale treated-control comparisons when many categorical covariates are present. The algorithm balances covariates and their interactions in a prioritized manner by solving a combinatorial optimization problem, and guarantees computational efficiency through the use of a sparse network representation. The second chapter defines a class of variables called prods which can be ignored when matching in order to strictly attenuate unmeasured bias, if it is present. These variables can be difficult to identify ...