Sorry but I think your examples are not based in reality. What you described is certainly doable yes, but it's a minority opinion. Very few people are taking their kids to school on a bicycle in January. Same goes for people hauling 200lbs of garbage anywhere. Also if riding in the winter were such an easy thing we'd see motorcyclists out in full force year round, but that's simply not the case. Two wheeled transport is not pleasant nor really viable for 4/5 months of the year here.
If you work in a foundry showing up at work looking like you crawled out of the alley is OK. In a prestige office environment not so much.
When I was a kid in Manitoba I walked 2 Kms to school in better weather, bused it in winter.
The first two years of Toronto high school were 3.4 Kms each way to school walking in better weather and TTC in winter.
The local school now has a parade of soccer moms dropping off their darlings who live a Km away.
The past prime Prima Donna down the street isn't going to wear her latest designer creation on the TTC, walk or ride a bike.
E bikes may suit some but they are mini motorcycles and not everyone is comfortable on two wheels. Mobility scooters may be better but they are wider and may need charge points.
Bicycle racks on buses just slow down the process.
Bicycles get stolen or abused unless in a safe lock up. Safe lock ups aren't everywhere. Don't expect the police to send out a SWAT team when you report your bike stolen.
Tourism: How many tourists will come back after being stuck in our bicycle gridlocks? I was trying to give a visiting American lady some directions to get her out of a traffic jam, pointing out that the next time she came things would probably be better. Her answer was "THERE WON'T BE A NEXT TIME. I WILL NEVER COME BACK"
My wife can't ride due to a bad knee so I built a sidecar for a bicycle so we could do something besides use ICE. The basic bike was steel framed, had a sub chassis of steel and a light weight car. Adding my toothpick wife and me we were over 400 pounds. We mostly did rail trails because trains don't like steep grades either. The front sprocket was about 6" IIRC. Try going up some of Toronto's hills. Try stopping going down them.
Chow and the councillors need to start out in Scarberia or Rexdale and commute to city hall every morning, rain or shine.
Change your job and lose your seniority. A lady my wife worked with used to spend an hour each way on the TTC to get from her Scarborough home to the office in mid Etobicoke. Then the office moved to south Mississauga and the ride was Go Train and Miss transit for an hour and a half each way. The company just moved again to south Brampton. She's at four hour a day on buses and trains. Fares aren't cheap. She doesn't want t lose her 20 years seniority and benefits.
She could move to Brampton but her hubby works in Scarborough and it would be him on the buses for four hours a day.
If she moved, the distance as the crow flies is under 40 km so the costs would be on her dime.
She may be a unique case but at some time or another we all will be. What about when we need an ambulance, fire truck or police car?
We have to fix public transit before we scrap the inefficient system we now have. It would be a miracle if that happened in 20 years.