A technician will usually check the burner, controls, low-water cutoff, pressure relief valve, circulator or steam vents, and the flue. In prewar Whitman homes, expect questions about how the piping runs and whether radiators have been removed or added over the years, since both affect how the system balances.
Replacing a boiler generally needs permits from the Building Department at Whitman Town Hall, which issues gas, plumbing, and electrical permits. Inspectors are scheduled by calling them directly. Old boilers may also come with asbestos-wrapped pipes; ask the contractor how that would be handled before demolition begins.
If you're considering a high-efficiency condensing boiler, the visit should include where the side-wall vent and condensate drain will go, and whether the old chimney needs a liner for any remaining appliances such as a water heater.