This section of the city between Spadina and Lower Simcoe is set to fail as a connection between the city and waterfront because there are no north/south roads. The Skydome and CN Tower alone make it impossible for a N/S link. The Convention Centre just continues that division right over to Simcoe. Unless Skydome and the Convention Centre are torn down, that strip will remain isolated and disconnected from the built-up city grid.
That said, I dont think it is a bad thing. This is Toronto's tourist "centre" The area is full of tourists even in winter, and provides what I think is the Best View of our city. Let the N/S connection be at Spadina, Simcoe, York, Bay, Yonge etc etc.
I think that connecting the waterfront with the city is best accomplished by having that "Bay Street canyon effect. A seemless connection of buildings, constructed right up to the street will guide people from the north all the way down to the waters edge. The Telus Tower, Res of Maple Leaf Sq, 18 York and the yet to be released building(s) set for the parking lot beside Infinity will make that connection. The waterfront doesnt start at Front, it doesnt start at the rail tracks. The Waterfront starts at Queens Quay. I am glad that the city has realized this and is building big, south of the tracks. Bring the city to the water, not the water to the city via endless parks and wasteland.