A repair visit usually starts with a combustion and safety check, then the pump, expansion tank, relief valve, zone valves, and controls. On steam systems, expect questions about when the water level was last checked and whether radiator vents have been replaced.
Replacement brings permits. Avon's plumbing and gas inspector covers gas boilers, and the Avon Fire Department covers oil-fired equipment and any tank work, with all of it filed through PermitEyes. Moving from a chimney-vented oil boiler to a sidewall-vented gas unit may also involve lining or abandoning the chimney.
Old basements can be tight. Ask how the contractor will get the old boiler out, whether any pipe insulation needs testing before removal, and how long you'll be without heat during the swap.