On an oil boiler, expect the technician to service or inspect the burner, nozzle, filter, and chimney or vent connection, then check the circulators, zone valves, expansion tank, and relief valve. If the boiler heats your water, they may test how much hot water the coil delivers and talk about descaling it or adding an indirect tank.
Oil burner work requires a Department of Fire Services certificate, and gas or propane boilers need a gas fitter. If the job grows into a replacement, Carver's Building Department takes gas and plumbing permits on paper, and the plumbing and gas inspector works Monday, Wednesday, and Friday, with the license holder calling in the inspection.
A good contractor will tell you whether the cast iron sections or heat exchanger are sound, which decides whether repair or replacement makes more sense.