You make an interesting argument, but I think (based on my own instincts and what I've read on this forum) that you're in a very, very small minority there.
'1984' is a horrifying dystopian novel about an extreme case of totalitarian government enabled by technology. 'Order of the Stick' is a mostly-lighthearted fantasy about an epic quest to save a world. Those two genres are about as far apart as you can get.
So - sure, Rich could buck convention by allowing a blatantly Evil-with-a-capital-E-no-matter-what-he-says-about-it villain to roam free. And the Oracle could be completely wrong about Elan's happy ending, and Belkar could join Tarquin's party and live another 80 years, and Xykon might lose interest in the gates and retire to torture souls on the Astral Plane and be taken out years from now by some wizard we've never heard of.
All of that could happen - but it's not going to. Do you think it should?