The answer is $ isn't it?
The answer is rarely money - freeways and ring roads are some of the most expensive stuff we build and we find money for those, speed bumps and raised crossings are hardly budget-breakers.
To me, the answer why we don't see these kinds of pedestrian improvements is a mix of transportation "standards" that resist change - meaning generally accepted design and building practices for the engineering profession, decades of city-specifications, Alberta roads, randomly applied fire truck and bus standard practices etc. - combined with typically very obtuse or non-existent feedback mechanisms for the public to influence how things are done on both the "standards" level or the local issue level.
I am not aware of any process where locals can just vote to put in speed bumps on their own street or raise a cross walk to a school so they can walk there. Even if you band together and raise enough noise to get a professional study done, the public doesn't have a say on the thresholds for when "acceptable" safety is achieved. Many possible improvements that would make neighbourhoods safer and more livable have died at this step because the standards say there's not really an issue as defined by them, ignoring that if we just built all local streets safer, slower, narrower in the first place you'd never even need to do the study.
This explains our reality - there's many Calgary-specific examples where the "standards" weren't applied, the roadways and road geometry was tightened up, traffic calming and cut-through speeding was eliminated. But it isn't applied everywhere, it's totally ad-hoc - a specific project with a strong vision that out-competed business as usual for a period of time (e.g. downtown cycletracks in the early 2010s), a specific politician with ongoing focus and energy to keep challenging standards to make things more walkable and safer (e.g. Kensington areas better-than-average success in getting traffic calming and nice sidewalks decades ago) several repeated safety tragedies caused directly by "business as usual" road design (Elbow Drive's famous 40km/h stretch) etc.
Luckily change is happening - standards are shifting and professional practices are moving towards more recognition of safety and walkability. Cycletracks are becoming standards themselves, just part of the process to look at when a road is being rebuilt. Those new main streets redesigns are top-quality, higher quality pathways and cycling facilities are proposed all the time now, 8th Street SW 5 to 3 lanes proposal, 11th Street SW pedestrian-only underpass, 40km/h standard v. 50km/h etc.
It's too slow of change - hence my endless pedestrian safety and design rants - but it definitely is changing positively.