Here is a PDF that the City of Oshawa published talking about everything you need to know for registering a Legal 2-unit dwelling in Oshawa.
In my opinion the 3+2 bedroom legal two unit dwelling is the perfect combination between solid numbers, ease of entry, and ease of management
The reason why condos and single family residential are such a popular investment are because of how easy they to get into and while that is true the major problem is the properties are not turning a profit, yes losing money each month. Investors are gambling that the market will go up and that’s how they will offset the negative cashflow.
On the other end of the spectrum you have multi-family properties which are 3 or more units, which can generate great cashflow with a great return on investment. They have a higher barrier for entry though because they are typically more expensive and will likely need more money down if you need a commercial mortgage. Also with a multi-unit investment, the tenant profile can be lower as well, making it harder to manage
The 1960’s brick bungalow is the perfect investment option because they are typically in quiet residential streets with large lots, separate entrances, and liveable basements that allow for a legal second suite.
The 60’s bungalow also has a low barrier for entry and a high quality tenant profile, but unlike a condo can give you high ROI. The reason you can get such a higher ROI is because you have the ability to add value quickly with the Buy Fix Refi Rent investment strategy.