One way I have thought about MacLeod is that it's kind of the poster child when combining 75 years with an distinct absence of urban planning and overly strict transportation design rules for arterials.
To get started: a central problem is that the properties are both two big and too small along MacLeod - too big that each one needs a bit of a comprehensive and multi-phase approach to build anything, however never big enough to create anything that's "complete" the way that an entire neighbourhood would be designed.
Usually this is where urban planning kicks into gear as it's concerned with the orderly development of properties and integration of all properties into a coherent plan, perhaps something that lays out the networks prior to development build out, encourages subdivision of the larger parcels to reasonable blocks, focuses land uses around key nodes or corridors etc. As far as I can tell that never happened on MacLeod in any meaningful sense. This leaves each development really just doing it's own thing and never trying very hard to align to an overall vision (because it doesn't exist), and makes it next to impossible to get things right like basic connectivity and access figured out between each development and to and from the MacLeod corridor to surrounding areas.
The most serious role municipal planning ever played in development here seems to be the strict interpretation of arterial policies for MacLeod and the connecting major roads. These restrict access, force development to never front onto the street, set aside enormous right-of-ways for expansion, and limit signals and intersections. The result of this treatment of MacLeod drives all the properties to further chaotic weirdness, because they can't create anything that integrates into a grid or has a walkable frontage with the main road - it's actively discouraged along MacLeod.
In short, we missed the turn-off to have a more planned and coherent corridor about 75 years ago and have essentially seemed to be hands-off ever since so each redevelopment project continues this weird, isolated and chaotic trend.
Why it stays bad is pessimistic and defeatist attitudes and entrenchment of status quo in decision-makers: lots of views engrained out there that MacLeod Trail can never be fixed, so why even bother trying anything. So the cycle perpetuates a new development happens of serious density and opportunity, but can never be big enough to overcome the defeatist inertia and strict policy rules that keep the street the way it is. The development is then forced to be an island looking inward to itself, fails to integrate to anything, and exacerbates the problem.
It's a stretch goal, but I'd love to see MacLeod Trail evolve into a Highway 7 in the GTA vibe (perhaps the towers are implausible, but my interest is more in how the buildings connect to the street rather than their height). Here they took an ugly MacLeod Trail corridor and made something far more organized and friendly to be on for all modes. And "war on cars" it isn't - Highway 7 didn't even try to give any of the car-orientation up (still 6 - 8 lanes + bus lanes).
Don't let those transportation engineers tell you otherwise - we don't have to live in sloppy nightmare of concrete barriers, fences, rough asphalt jobs and dirt medians. Not all car sewers have to be this dysfunctional and ugly!
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