The Metz (Schneiders site redevelopment)

[taylortbb]

There are, or have been at one time or another in the past, many commercial uses along the other side of Courtland between Borden and Stirling.

Sure, we have lots of things in our cities that aren't allowed to be built by today's zoning. The past commercial might make the city more receptive, but I expect neighbourhood objection would be fierce.

They have the zoning they need for the property. But I don't see how Courtland (assuming this is the proposal) would work well as the only road given how deep the property is.

I didn't interpret "main street" to mean only street. I think a development of this size obviously needs internal streets. My interpretation of the question is, why is the "main" street, with all the commercial, always buried inside the development. Putting all the commercial along Courtland would likely make it far more visible, and therefore likely far more successful. Being "on the way" is incredibly valuable for a small business. Given I assume successful retail is more profitable, I doubt developers sabotage their retail intentionally.