I agree, that our Waterfront will never look as stunning as other major world cities, but you must remember that Toronto is a World City wannabe. Toronto citizenry and it's politicians are timid and have a small town mentality. It prevails across Canada. Toronto's current mayor is the epitome of cheapness. If it was up to him we wouldn't be 'wasting' any money on any waterfront improvements. The work that has been currently been done will be the best public space that Toronto has. Compare the quality of Queen's Quay, Sugar Beach to the Bloor Street transformation. These are all small slivers of public space, but at least the new waterfront areas are going to be connected and will have a waterfront promenade with mature trees.
Toronto can never get Chicago's waterfront, but frankly I wouldn't want it. Chicago's is great for tourists who travel there, but in my view, outside of Millennium park, the waterfront is fairly bland and tacky also. Sure it's got great museums, but it's meant for tourists not locals. Plus, there is not much to do in Chicago's waterfront area except to stroll around. There aren't any restaurants outside of Navy Pier.
Toronto needs to define it's own identity. We will have a dense waterfront and the new East Bayfront neighbourhood I am hoping will define us. If it is built well, we may have a fantastic waterfront street lined with patios and restaurants. Our waterfront will be busy, happening, and it will become a local destination. Toronto was never destined to be a tourist town, but our waterfront will be just that, it will be for Torontonians to use and enjoy. I hope that the improvements continue after the current set of projects, since Waterfront Toronto is due to run out of money in 2017 and will need a progressive mayor and council to let it borrow money against future construction so it can continue it's great work to date.
I'm excited to see the East Bayfront completed and Queen's Quay boulevard remade. If the same change gets applied to Queens Quay East, we will have a beautiful main waterfront street compared to the ugliness that it was before the transformation.