Mercule said:
Yet, in every discussion of alignment, it always comes up that Chaotic characters are a bit off, when compared to Lawfuls. Either they are assumed to be inherently less sane, less virtuous, or just plain more troublesome than Lawful characters.
I'd say they are all those things, depending on your definitions of sanity, virtue and troublesome

Most societies, themselves being Lawful constructs, value Lawful tenets over the long run: stability, order, peace, security, etc.
The young musician who struggles at a series of dead-end part-time jobs because otherwise there's no time to practice, to sit and think and write, to work out that
sound that keeps evading him and find a way to express it... yeah, he's less 'sane' than if he'd gone to business school, worked hard and impressed the right employer and wound up with a corner office at 25 is 'sanity' is seen as maximizing your opportunities. Even if he is successful at a music career, he'll probably always live hand to mouth unless he's one of the extremely lucky. He's not secure; if he's moderately successful he encourages others not to be secure and stable. There's a reason that until just recently actors and musicians were seen as barely respectable bums who were best kept away from decent folk.
Virtue is a construct of a lawful society, part of set of artificially exalted do's and don't's. The handsome dandy who has a series of male and female liasons, doesn't keep regular hours, flaunts the conventions of a community and gets away with it all certainly doesn't conform to most views of 'virtue'. The lawful person will usually conform to the conventions of his community provided they don't conflict with other things (the lawful good person will not conform to the hobgoblin community practice of killing someone who looks at the king without bowing, for instance).
The gadfly who plays the Devil's Advocate just to point out foolishness, sweetheart deals, inordinately complex and Byzantine laws - not to root out corruption or wrongdoing, but simply to point out that things don't have to be done in a rigid staid manner is certainly a troublemaker. The Lawful person would welcome almost any increase in order, even order for order's sake.
I guess one reason that the 'CE unable to pull off this huge plot' thing rackles is that people who pull off huge plots to cause massive evil all at once have generally been characterized as Chaotic Evil, which for so many years has been seen as 'the worst evil'. Got a bad guy who is going for the over-the-top massive death raise-everyone-in-the-city-as-a-zombie-slave plot? 'Wow, that's just beyond Evil, so make him CE 'cause that's the worst evil there is!'
It's not. Neutral Evil is.
Lazy writers who possibly didn't even really look at the alignment system have made a lot of people think that CE is something it's not.