I mentioned this very thing to a city official after struggling to find information on the Toronto.ca website and they chuckled when I told them I have been a web designer for 26 years with a heavy emphasis on UX and I felt stupid not being able to find such simple information. I said I should get a job there to fix all this. With a smile in her voice, she said "You should" with a long pause like she wanted to say more.
Anyway, they are horrible for upkeeping the website. Relevant information is not updated promptly.
Example: The Cherry House Affordable Housing Lottery that is up on the Toronto website now. It ends on December 1st. Watch how long that information stays on that page past December 1st. Before that, the last lottery was up for at least 4 months past the end date.

Literally simple scripts can simply have that information vanish from a page on the end date or even setting a note in an email calendar to remove the info would also work.
As a result, I'm never sure if I'm reading any information that is current on any of the city websites (Toronto.ca, CreateTO, etc).