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Well, you chose a weird fall/winter picture for St. Louis looking towards the East in the area heavy with parking lots at a lower angle and more zoomed in to see those parking lots, while you chose a spring/summer viewpoint of Winnipeg that comes from across the riverfront at a high vantage point so the surface lots aren't as dominant in the picture and the weather and lighting look nicer.
That is an ugly picture of St. Louis and a attractive picture of Winnipeg. I don't know that Downtown St. Louis photographs very well from around Jefferson looking east with no greenery.
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