We study a one-dimensional discrete nonlinear Schrödinger model with hopping to the first and a selected N -th neighbor, motivated by a helicoidal arrangement of lattice sites. We provide a detailed analysis of the modulational instability properties of this equation, identifying distinctive multi-stage instability cascades due to the helicoidal hopping term. Bistability is a characteristic feature of the intrinsically localized breather modes, and it is shown that information on the stability properties of weakly localized solutions can be inferred from the plane-wave modulational instability results. Based on this argument, we derive analytical estimates of the critical parameters at which the fundamental on-site breather branch of solutions turns unstable. In the limit of large N , these estimates predict the emergence of an effective threshold behavior, which can be viewed as the result of a dimensional crossover to a two-dimensional square lattice.