It makes sense when you realize Ford won't do anything that returns private money to the public, but will do everything and anything that enriches the private sector.
Removing tolls from the 407 would be a public benefit, so he won't do it. You'd be more likely to see him sell the east-of-Pickering chunk of 407 for a "tax break" and claim it's a win.
The reason citizens feel this way is because they've seen the half-assed policy we have, where we don't enforce drug laws, but don't support addicts either, and the result is serious harm to just about any city of size in most of Canada.
The correct solution would be a) housing and comprehensive supports for addicts, so they have a roof over their head and can get clean, b) safe-supply, and c) actual enforcement of laws and bylaws so that the only place you can use your safe, free supply is the home from a) or the treatment centre in b).
All of this would cost money and political capital. The cheap solution was to just do a half-assed job enforcing laws about drug use, and a similarly half-assed approach to the crime caused by drug use, with a token few bucks thrown at safe-consumption. This looked wonderfully progressive, and it had the benefit of being cheap and keeping the riff-raff out of nice suburban spaces. Basically, we looked at Portugal's solution, and did maybe 30-50% of it, and looked all shocked when it didn't work.
Now we're dealing with a situation where we didn't address the causes of addiction, and piled on not addressing the impacts, either. And people--voters, people who live and work in downtowns scorched by addiction--are unhappy about it. And now it's a more expensive problem then it was 10-15 years ago.
This is painfully typical of Canada: ignore a problem when it's cheap to fix, half-ass a solution, and then cry poverty and powerlessness when the problem metastasizes into a crisis. See: healthcare, education or immigration
Singh et al learned absolutely nothing from the Harper era