The district's biggest advantage is lot width. Many post-war lots are 40 to 50 feet wide, which leaves room for four real units without the side-yard squeeze of the old city. The first question is usually not whether four units fit, but how best to arrange them: stacked, side by side or a mix.
The second question is trees. Mature oaks, maples and boulevard trees are common, and Urban Forestry protects many of them. A tree protection zone can shift the building, change the foundation design near the roots or limit where equipment can go. Bringing an arborist in at feasibility is cheaper than redesigning later.
Third, check the water service. Many 1950s and 1960s homes have small water lines that cannot carry four units. Upsizing usually means a road cut and a separate permit, which runs on its own timeline. Filing it with the building permit protects your occupancy date.
Fourth, be clear about the unit cap. The district is outside the approved sixplex areas, so four units is the as-of-right maximum. On deep lots, a garden suite can sometimes add a fifth home legally, which can also change your financing options.
Finally, look at transit. Lots near the Yonge Street corridor and TTC Line 1 stations may fall in Major Transit Station Areas, where parking requirements can be lower. That can free up space on the lot for units, landscaping or bike storage.