Get most StackOverflow rep by avoiding difficult questions
If you look at my top-voted answers, they all seem like things where someone either doesn't understand a basic concept, doesn't read available documentation, or hits an error message and drops it directly into Google without considering the issue on their own. It's an interesting phenomenon, and I wonder if it's a observation for other users. I have really simple questions that still get me 1-2 upvotes a month for years after the answer was provided.
If the answer also happens to be for a popular language/framework/n00b problem, then all the better.
Ex: http://stackoverflow.com/users/249543/jefflunt
If this is common, then it would seem a reasonable strategy to just look for easy questions and answer them quickly - if the only reason you're on SO is to play the reputation game, that is.
This supports my general view that, if you want a decent chance at running a business that will have a large client base, simply take a problem that is very common, but not very difficult (maybe trivial) to solve for an experienced person, and sell an automated solution to the masses.
When a really tough question comes up, it probably effects only a few people, so only few people will upvote. I'm assuming 'tough problem' comes up only because something new and unusual is being attempted.
It happened to me in several occasions. And this is one of the reasons I tend to avoid answering questions now.