Well you've pretty much summed up the funding issues and that's my point, we ignore the issues that we face until it becomes extreme. Which is pretty much John Tory's mantra: delay, defer, put on the approved but unfunded never ending list of projects, and beg upper levels of government for funding. By the time we get to addressing said problem, it becomes magnified even more and the state of affairs is worse than it initially was.
That's the problem we've been having in this city for 8+ years, and it's a big reason nothing ever gets done. If something actually does get done, it takes eons because we cant fund anything or our "leadership" genuinely is unable to come up with a solution.