I actually have a slightly different take on the Toronto waterfront. I think its best parts are hidden. The accepted wisdom on the central portion is largely correct, I think: It IS cut off by the Gardiner, and its amenities, while improving, are pretty mediocre. Maybe this has to do with working for years in the Toronto Star building, where the view from my office window was this:
Yeah, the Harbourfront Centre and whatnot are there, but in terms of the overall stuff to see and do, it's a bit bleak. And Queens Quay is a truly dull canyon of 90s condo buildings.
BUT, so many other parts of the city interact incredibly well with the lake, but we don't think of them as "the waterfront": the Scarborough Bluffs, the Beaches, the Leslie Street Spit, the Toronto Islands, the Martin Goodman Trail, Sunnyside, Humber Shores, Sam Smith Park, and on and on. There are so many great landscapes and neighbourhoods along the lake, and interestingly, many of the best parts of the waterfront (the Spit, the Islands, the Bluffs) aren't particularly urban, but a bit wild and unkempt. It feels...Canadian. Not manicured, but probably a lot more interesting. So yeah, while I think the generally accepted wisdom is correct (i.e., the downtown waterfront is meh), I think that a lot of people, especially tourists, just don't think of, or aren't aware of, the rest of it.
It's the opposite of where I live now, in Halifax, where the downtown watefront is a really well put-together boardwalk stretching for more than a mile, from the historic district to the city market. An unbroken stretch of marinas, playgrounds, parks, food vendors, bars and restaurants (including some very good ones, not just tourist-oriented junk, though there's lots of that too) and even some recent condo developments that work pretty well in context. And, of course, it overlooks a pretty stunning natural harbour.
But outside of downtown, almost all the city's waterfront property (except along a few parks, and some private property in more well-to-do areas) is industrial and inaccessible to the neighbourhoods adjacent to it. I like that our downtown waterfront is such a success, and so attractive to locals and tourists alike—it'd be pretty embarrassing as an oceanfront city if it wasn't. But I do miss a bit the way that Toronto's waterfront, along the more distant eastern and western flanks, feel like extensions of the nearby neighbourhoods. But because they're not central, they're overlooked.
EDIT: I just saw NouvelleEcosse's comments on the Halifax watefront--I'd say that the parking is a necessary evil, since let's be honest, the area attracts a lot of tourists from out of town or rural areas, and it'd be a losing battle not to provide parking. The parking isn't right up against the water, and really, I rarely notice it when I'm down there. Plus, a lot of it is slated for redevelopment now. There are ways it can be improved, but I think it's fantastically successful as-is.
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