I think it has more to do with it being run into the ground for the decade or so since his departure. Paul Martin wasn't good for the party structure. Neither was Dion. And Ignatieff didn't have a clue what he was doing.
I think the key to being electable in politics these days is to have intelligence, but to also be able to relate to the commoners. Chrétien was really good at that. Now having said that, he also benefited from the same type of split opposition that Harper is benefitting from now. I believe that most of his majority governments (if not all of them) were won with under 50% of the popular vote. However, because the right was split in much the same way that the left is today, he was able to get elected with a majority.
Dion and Ignatieff both failed in the same area: communication of their ideas with the general public. Those who were interested in the topics and bothered to do any actual research saw the merits of their ideas, but the average Joe read the headline and was instantly against them (NeoCon attack ads didn't help).
I do think it is harder for politicians on the left to get their ideas across though, mainly because the ideas are so much more complex, and a lot of the time they require looking beyond what you yourself need, and looking at the greater good of society. Conservative ideals play to our baser instincts ("What's mine is mine, and don't you dare try and take it from me. Work for it yourself."), and thus are much easier to explain. Every problem is a lot simpler when you only have to take care of your own interests. It's only when you start to take into account what other people may need too that problems start to seem more complex (or in many cases, start to appear closer to what they actually are).
You actually think there's a possibility that Ford could be re-elected? Have you seen his approval ratings? Never has a mayor's approval fallen so quickly, so fast. It took Miller 6 years and a garbage strike to get that low. Ford seems to have gotten there already, but in order to make it even lower, he seems to be trying to create another garbage strike. Ford was elected because he convinced many that there was too much waste in government, and that the could eliminate the waste and taxes without cutting services. Ford was elected because he wouldn't cut services. Many people believed that. After 4 years of cuts and constant threats of more cuts, I can't imagine that many will fall for that again. Unless the next 2.5 years are radically different to the first year, I think Ford has little chance to be re-elected. And to bring this back on topic, I'm not even sure he will have the support of council to proceed with his Sheppard subway gravytrain.
Never underestimate the ability of NeoCons to create a reality distortion field. Facts are only facts if they support their ideology, if not they're lies concocted by the liberal elite in order to spread socialist ideals. We live in a sound byte society. Whoever can come up with the best idea (grounded in reality or not) that fits into a catchy sound byte will likely win over a significant number of people. Unfortunately, the right pretty much has exclusivity over this territory, as sound bytes like "stop the gravy train" are much more appealing to the average Joe than "we need to continue with the various policies and plans that have been laid out in the City of Toronto Official Plan". The former resides in the gut, the latter resides in the brain. For a lot of people, the brain doesn't even factor into the voting equation.
Ford actually made people believe that the city was drowning in debt, and that the budget was spilling red ink anywhere. The facts didn't seem to enter the equation at all. Will people be smarter come next election? I hope so. But never underestimate the power of a good spin.