We analyze a classification of two main families of controllers that are of interest when the feedback loop is subject to switching propagation delays due to routing via a wireless multi-hop communication network. We show that we can cast this problem as a subclass of classical switching systems, which is a non-trivial generalization of classical LTI systems with time-varying delays. We consider both cases where delay-dependent and delay-independent controllers are used, and show that both can be modeled as switching systems with unconstrained switchings. We provide NP-hardness results for the stability verification problem, and propose a general methodology for approximate stability analysis with arbitrary precision. We finally give evidence that non-trivial design problems arise for which new algorithmic methods are needed.1