I'm fairly confident in the Portlands redevelopment. There's substantial developer interest, and Waterfront Toronto is quite competent at achieving our waterfront goals. The only thing I have a big doubt about is the arrival of the East Bayfront LRT.
One only has to look at how much the Waterfront Toronto plans were scaled back (either in timeline or in scope) after the 2008 Olympics were awarded to Beijing instead of Toronto. Yes, they did eventually happen, but the timeline was much slower, and they didn't have nearly as much funding available to them as they would have had that bid been successful.
I think Expo is a bit different though. Before we had a big plan that had to be scaled down after a failed bid. This time we have a pretty substantial plan that would need to be scaled up in the event of a successful bid. Tighter timelines and increased attention would mean more funding for a grander plan. It would certainly push the East Bayfront LRT from the "yeah, we'll get around to it" column to the "holy crap we need to get on this" column.