The first thing to confirm in the district is the ward. Inside Ward 23 North, six units can be permitted. Everywhere else here, four is the maximum. Because the boundary runs through neighbourhoods, it has to be checked for the exact parcel, not assumed from the area name.
Second, decide between rebuilding and adding. Many local bungalows sit on wide lots with sound foundations, which makes a basement unit plus a second-storey top-up a strong option. Others are better replaced with a purpose-built fourplex. An engineer's view of the footings usually settles the question.
Third, if you are in Ward 23 North and thinking about six units, look closely at the lot shape. Corner lots and wide lots can carry the second exit stair, bike storage and separate entrances a Part 3 sixplex needs. Our Ward 23 North sixplex worked because the corner gave room for all of it.
Fourth, check for the Bluffs and the creeks. Lots near the Scarborough Bluffs or Highland Creek may fall under conservation authority regulation for erosion and flooding, which limits where you can build. Near the lake, 316 stainless fasteners belong in the specification.
Finally, plan for family. Many local projects include parents or adult children, so accessible ground units, separate utilities and private entrances are worth designing in from the start. They also keep every unit rentable later.