The contractor should visit, size each room, and suggest indoor unit types: wall-mounted heads, ceiling cassettes, or a small ducted unit for a couple of rooms. Expect a discussion about line set routes, where the condensate drains, and where the outdoor unit or units will sit.
Rockland's Building Department, which includes the wiring inspector, handles the permit side, and applications can be filed online. Inspections don't happen on Fridays. If the project also takes an old oil burner or tank out of service, that piece needs a Rockland Fire Department permit.
A typical install involves mounting the outdoor unit, drilling a small opening for each line set, hanging the indoor heads, running power, and testing the system. In older Rockland houses with plaster walls, ask how the contractor will route lines neatly, often with exterior line set covers.