A contractor typically starts with a walk-through and a heat loss calculation, looking at insulation, windows, and which rooms are hardest to heat. In a radiator house without ducts, expect a proposal built around ductless or short-run ducted indoor units; where ducts already exist, a ducted system may use them.
Permits depend on the scope. Inspectional Services at 525 Canton Avenue enforces the state electrical, sheet metal, and building codes, and removing an oil tank or burner goes through the Fire Department on form FP-056. Ask the contractor to list each permit in the estimate.
Installation itself involves setting the outdoor unit, running refrigerant lines and drain lines, mounting indoor units, and wiring. Plaster walls in older Milton homes can affect where line sets run, so ask to see the planned routes before work starts.