I was elected as an underdog in the 2011 election, in fact the first Stack Overflow election to utilize our built in moderator election system (other smaller sites had used it previously). I also didn't think I stood much of a chance of being elected, after all, I only had a small percentage of the reputation points that everyone else had.
I barely made it out of the nomination phase as the low water mark continued to rise. I wasn't just competing against people with high reputation scores, I was competing against people that weren't half as serious as I was about doing the job with higher reputation scores. Even at that point in the site's history, I had invested a great deal of time and thought into what we were building, and I really wanted to get in a position where I could be more effective.
If it hadn't been for the primary phase, I probably wouldn't have been elected. This was the junction where people could seriously consider who was capable, and apparently enthusiastic about doing the job. This really helped move them ahead in front of those that might just be after a little more bling on their user card or a peek at the extra privileges.
Things are different today. The system now presents you with a much better picture of each candidate as a whole, we have a third party election app created by the community to help folks make more informed decisions. And, in this particular election, we saw an amazing turn out. I want to vote for almost every single person that nominated this time - but I know I can't.
Ten of those very awesome people will advance to the final election phase, which means (in this election), we're likely to have a 100% chance of picking the right moderators, as all of them should be fantastic candidates.
We must make certain that those who enter the final phase are capable, serious and passionate about doing the job; this process does quite a bit to ensure that. A lot of eyes fall on every single person that might make it to the next phase - this works extremely well. You might even see some folks withdraw - the process isn't for the faint of heart, and neither is the position itself.
I don't think any system of election is perfect, at least not one that I've ever studied, but our's works pretty well. It helps alleviate option anxiety, which is important, but it also helps to guarantee that someone that isn't really all that serious moves on to get elected.
I don't think you asked a bad question, if elected you're definitely going to run into more things where you wonder how these crazy people came to do things certain ways. Nothing but dusty old moderators and hipsters on this team, and you seem to be heading straight at working with us :)