The South Atlantic Bight Synoptic Offshore Observational Network (SABSOON) was initiated in 1998 with funding from the National Oceanographic Partnership Program (NOPP) to establish an oceanographic and marine meteorological monitoring program based at a set of Navy platforms on the continental shelf 50-100 km off Georgia. The program is a partnership between several academic institutions, two federal agencies and a state agency. Observations have been collected since 1999. We will review the status of the system and consider the lessons learned about operating an offshore monitoring system over several years. A number of factors influence our ability to regularly collect and distribute near real-time observations, including access to the offshore structures, reliability of power and communications systems, availability of personnel, ruggedness of sensors and sensor deployment systems, and susceptibility of in-water measurement systems (especially optical sensors) to biofouling. Recently a data assimilative modeling effort, also funded by NOPP, has been developing a nowcast/forecast system for a limited area of the continental shelf that relies in part of observations from SABSOON. Results from initial assimilation efforts, and implications for the spatial density of observations required to constrain solutions, will be discussed. All these factors are relevant to developing an operational, sustained observing system, and have implications for realistic funding levels required to achieve this goal.