Other cities, some smaller than Toronto, have buried their obtrusive 60s infrastructure years ago, but somehow we "can't afford it."
 
I have a question about the ‘islands’ surrounding the piers of the bridges. Are they meant to be submerged? Will they
be accessible? Sunbathing? Only meant for turtles?

The peninsula extending south under the Commissioners St bridge will eventually support the footings of the second bridge, dedicated to transit (like with North Cherry St). It will remain above the water level, and I imagine it will be accessible to recreational paddlers?
 
What's the plan again for how they're going to do that and keep the connection while they do the work? Are they going to build the new ramps first and then connect them and then demolish old?
This page has all the info I know about the Gardiner east realignment. Here’s the environmental assessment that shows the design alternatives, from which the council approved the hybrid 3 design. Since then (Nov 2017), haven’t heard any news. It might need a reassessment at this point.

For hybrid 3 design I’d like to see the two-lane DVP ramps hugging even closer to the Don Yard and preferably with less elevation. I think I saw a proposal somewhere to put this section on a berm instead, which I wouldn’t be against.
 
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A little love for what is now the dumpiest bridge in the Portlands! Lol Lime green is a logical choice and I am partial to F&B’s Danish Lawn. And some views of the Ship Channel which may, in the long-term, be a bigger opportunity than the Keating Channel. I know that in Belgrade the river is lined with boats that house bars and cafes that instantly turned neglected industrial space into a thriving and desirable area. Taken 11 February.

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