On a repair call, a technician will usually check combustion, the circulator and zone valves, the expansion tank, the relief valve, and the controls, and look at how the boiler vents. If you're considering replacement, ask them to look at the baseboard lengths in each room, since that affects how low the water temperature can go and how well a condensing boiler performs.
A replacement is permitted through the town's PermitEyes system, and the plumbing and gas inspector checks the work. The inspector keeps limited weekday hours, so inspections may take a few days to book. If the old boiler vented into a chimney that a water heater also uses, the contractor should address what happens to the water heater's venting.
If you're planning to sell, remember that the Randolph Fire Department's smoke and CO certificate inspection is required for a sale, so make sure carbon monoxide alarms are in place near the heating equipment.