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I have never seen a city with so much ugly surface parking as Hamilton ... Do you want to walk past this? There is absolutely nothing attractive.
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I noticed this too, the downtown is quite the car park. Imagine the amount of land that could be used for other things if there were a few multistorey car parks or subterranean car parks were built and those surface ones were used as green spaces or plazas or useful buildings were built on them. I remember visiting a square in San Francisco, I forget the name of it, but it used to be all parking. Then they buried the parking underneath and built a piazza above ground and that's actually very pleasant now and they still have the parking and it's hidden.
Referencing other threads, consider the uses of the land near the Hunter Street GO if that car park near to it were available for an alternative use?