Dynamic shifts in fleet structure and gear usage lead to complex implications for representing fishery selectivity in stock assessment models. There is generally a lack of consensus on how assessment models should be configured to confront changes in fishery fleet structure or associated selectivity forms, while balancing complexity-parsimony tradeoffs. We conducted a simulation analysis to evaluate the performance of alternative assessment models when confronted with fleet transitions among gear types, which included differences in (1) rates of transition (i.e., a fast or slow transition among gears), and (2) selectivity forms for each modeled fleet (i.e., asymptotic or dome-shaped). In general, explicitly modeling fleet structure (i.e., multi-fleet models) performed well, but demonstrated bias in biomass estimates and management reference points when selectivity forms were mis-specified. Single-fleet models were only unbiased when time-varying selectivity (e.g., using time blocks or continuous formulations) was estimated to account for changes among gear types. Our results suggest that single-fleet models with time-varying fishery selectivity are adequate for operational management advice, but research oriented multi-fleet models should be used as validation tools to explore model consistency within single-fleet models.