A typical visit includes checking refrigerant pressures, testing the capacitor and contactor, measuring airflow, cleaning the condensate drain, and inspecting the outdoor coil. Near the water, ask the technician to look closely at the coil fins, the electrical disconnect, and the mounting hardware for corrosion.
If the system needs replacing, the contractor will usually need an electrical permit and, if ducts are changed, a sheet metal permit, both filed online with the Building Department. The issued permit has to be picked up at Town Hall and posted where it's visible from the street before work starts. In a flood zone, the Building Commissioner may need to review where the new condenser goes.
For a seasonal home, ask whether the contractor can do the visit while you're away and how they'll get access, and ask for a written summary of what they found.