Fort Massey might be older, but I do think it's attractive. The windows on the top floor cap it off nicely, it has a little plaza out front, and solar panels!

I don't mind concrete as an exterior cladding at all. I'm actually not a huge fan of the Harbourfront Marriott - it's sprawling, bland (IMO), and acts as a huge northern wall to the boardwalk. Even if the boardwalk does continue past it, the hotel contributes nothing - if I remember correctly, it's simply a concrete wall lined with benches and lamps. To me, it marks the point where the waterfront boardwalk gets a bit uninteresting.
I agree with you on Purdy's. I don't mind the Sacred Heart addition, it looks handsome enough for its purpose (nice and simple) and I don't know that we would've seen anything terribly interesting built there otherwise.