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We used to park near the "Hooker Harvey's" back when Maple Leaf Gardens was still hosting the Maple Leafs. Maybe we were younger and more carefree, but there was a nasty hooker/druggie element around there 20 yrs ago. Queen and Sherbourne, Dundas and Sherbourne, Allen Gardens, yes there are some less than ideal areas east of downtown. It's not a large area though.
In general, speaking from someone born and raised in Toronto, it's not the immaculate, generally safe place I grew up in anymore. Yet the outskirts of the city are sometimes more notorious, Jane/Finch, Kipling/Albion, Birchmount/Finch.