The Toronto waterfront could get a “smart city” makeover as part of a redevelopment plan being spearheaded by Sidewalk Labs, a division of Google parent company Alphabet. The plan could also bring a new headquarters for Google Canada to the country’s largest city. Meanwhile, Toronto is also one of dozens of North American cities vying to be the site of Amazon’s second headquarters . During a recent segment on  Knowledge at Wharton’s SiriusXM show , Billy Fleming, research coordinator of the Ian L. McHarg Center at the University Pennsylvania School of Design, and Pamela Robinson, an associate dean of Graduate Studies and Strategic Initiatives at Toronto-based Ryerson University’s School of Urban and Regional Planning, discuss what Toronto has to offer Google, the infrastructure challenges the project would face, and how Google’s choice might shed light on Amazon’s decision about a new headquarters site. Additional coverage: The Headquarters Checklist: How Do Companies Pick a Location?…