Remember I talked about three D's? Well, I think gutter cleaning could fit all three of them. You have to reposition the ladder many times, you can fall off them and the job is definitely dirty. This sounds like a perfect job for a robot to me.
Although the justification of robot's application for this job is quite clear, at the moment I am aware of only one gutter cleaning robotic solution. That would be Looj made by iRobot.