I'll start: Toronto, Canada.
It is sooooo frickin cold up here. I can't wait for winter to be over. As a kid it was my favourite season. As an adult the traffic is godawful when it snows, plus I have to walk to campus through the slush and I don't have proper winter boots that don't leak.
My dollar sucks compares to my neighbours down south, which is horrible whenever I buy things, but kind of good when I sell things (on CK mostly )
I will never be able to afford property in this city as a Millennial.
Other than that, Toronto is nice.