We investigate the impact of packet dropouts due to non-idealities in communication networks on the performance of optimally derived controllers and observers in a minimax sense. These packet dropouts are modeled by discrete constrained switching signals via directed graphs. We consider time optimal control and estimation, minimum energy and fuel optimization and LQR problems for systems subject to packet dropouts which turn out to be combinatorial; and compute algorithmically the worst case performance of these optimization problems. To reduce the computational burden in solving these combinatorial problems, a partial order is imposed on the switching signals. Validation of the proposed methods is done over a set of randomly generated systems. Finally, by associating the worst case performance for each optimal control problem to the underlying network, one can optimize among the set of available communication networks.