Canada

It's a little annoying how this was a lesson the Greens have had to learn twice. Elizabeth May ran repeatedly in her relatively Green-hostile home town and lost every time, but at some point, she and the party agreed that if we were going to get a seat, they'd have to do it by putting our leader in a riding she was likely to win. So, the party did a bunch of polling, and May uprooted her life and moved to Saanich Gulf Islands... where she's won every election since.

We can't just pick a leader — no matter how good he is (and he's pretty great, check out his Wikipedia page), and expect that he can run and win wherever he is. Not in this electoral system and not with the Green profile where it is. Any candidate interested in actually winning needs to be willing to move their life to a riding where they at least stand a chance. Maybe there's a soft (preferably Québéc) seat somewhere, but Outremont clearly isn't it.