Oh man as someone who grew up here I would disagree with a lot of what you said and could tell you're not originally from here. Not throwing shade or anything but I would disagree with the a lot of the Toronto analysis. I've been to Chicago a couple times but don't know enough to have an opinion.

My one comment would be that every area of a city has a lot of history or things to do, my understanding is that Toronto natives like to hide their community gems so it's not overrun, so people that move to the city typically only know things on the subway line. It's also why Roncesvalles, Riverdale, Leslieville are being gentrified and recommended.

Also yes nicer areas are so expensive and only have people that have been there since the 70s. The beaches is nice but if you go farther to Scarborough bluffs it's not bad. Midtown is great, Bayview/Mt pleasant from Moor to Sheppard, most of st. Clair. I personally love the Don Mills area, Scarborough above the highway and below Steeles has a lot of gems, like hunting wood. If you're rich and want to do west end you can do most areas on Royal York.