We study a prototypical model of two coupled two-level systems, where the competition between coherent and dissipative coupling gives rise to a rich phenomenology. In particular, we analyze the case of asymmetric coupling, as well as the limiting case of chiral (or one-way) coupling. We investigate various quantum optical properties of the system, including its steady-state populations, power spectrum, and second-order correlation functions, and outline the characteristic features which emerge in each quantity as one sweeps through the nontrivial landscape of effective complex couplings. Most importantly, we reveal instances of population trapping, unexpected spectral features, and strong emission correlations.