However, as the tables in this article show so clearly, one task can dominate others. This serves as a great illustration of a perception problem the above strategy can create. Outside observers watch your progress and will probably evaluate it in terms of number of tasks completed.
You have (say) 10 tasks to complete, and from their point of view, all they know is a really long time has passed and you haven't even completed 1 of them! Since they are further removed from the situation than you are, they are almost guaranteed to not appreciate why the variable task is that way. They're likely to just think your team is performing badly.
So, maybe it's better to order tasks so that risky stuff is spread more evenly across the timeline of the project. It could create less confusion. Putting risk at the beginning is a strategy that requires a whole lot of trust and buy-in.