A technician typically checks the thermostat, filter, blower, coil, condensate drain, refrigerant pressures, electrical parts in the condenser, and the temperature drop across the coil. Adding refrigerant without finding the leak is a short-term fix, so ask what they found.
In a Milton house with an attic air handler, expect the contractor to need clear access through a hatch or pull-down stairs, and the visit may take longer in summer heat. For a replacement, ask which permits apply: Inspectional Services at 525 Canton Avenue covers the sheet metal and electrical codes.
If your system is old or undersized, the contractor may suggest a heat pump instead of a straight AC replacement, since it cools the same way and can also heat. Ask for both options in writing if you want to compare.