I'd say that OotS is one of those rare stories that could "pull off" a villain winning, given that the very concept of the story is that it's mimicking a roleplaying campaign. When the BBEG is just too powerful for the PCs and the PCs are unreasonable enough to choose a direct confrontation too early (relatively speaking) in the campaign, it can very well end up in TPK and that should be "acceptable" to the reader...

By now, though, I have to admit I'm sure it'd be very unsatisfying to 99% of Rich's readership if the story ended like that (and it'd be contradicting the Oracle's prophecy about Elan's happy ending).

But back then, say in the early #0100s, Rich's gag-a-day online campaign strip easily could've abruptly ended with everyone dying @ Xykon's throneroom.