We present analyses of linguistic features undergoing change in South Eastern Ontario, Canada: stative possession, deontic modality, intensifiers, and quotatives. The largest urban center of the country (Toronto) and three towns outside the city are analyzed from the comparative sociolinguistic perspective. Parallel frequency and constraints are found in changes with a time depth of 200 years or more, corroborating the parallel transmission of complex systems over time and space. However, changes that began more recently show marked differences across communities. While the youngest generations in the small towns have appropriated the incoming forms, the accompanying suite of functional constraints found in the urban center is absent. This confirms that diffusing changes do not perfectly replicate the model system. There is, however, notable divergence within patterns of diffusion. The expanding changes exhibit varying configurations, depending on the community, its founders, and the stage of development of the change. The results suggest that increasingly complex contact situations will continue to expand the possible outcomes of diffusion.