The level of realized positive impacts from computer-assisted scheduling and dispatching (CASD) systems depends on the specifics of each implementation plan and the overall deployment strategy that is contemplated early in the procurement process. Moreover, with increasing numbers of local CASD system implementations, state departments of transportation have only recently realized the need to incorporate feedback from paratransit providers in developing statewide strategies regarding future deployments of such systems. While considering the variety of needs of Illinois paratransit operators, this paper develops three different CASD deployment scenarios: a centralized, a decentralized, and a regional deployment. The consensus from a focus group was that a hybrid approach that combines the strengths of the decentralized and regional approaches should be further pursued. The total cost of ownership for the preferred alternatives is also developed.