Another way of looking at it is that "I could care less" (or "I should be so lucky", etc.) is a truncation of a disbelieving subjunctive. In other words, it's short for something like "If I could care less, then I could fly to the moon", except that the speaker doesn't finish the thought.
I'll add yet another line from the quoted source:
And because it is hard to be sarcastic in writing, it loses its force when put on paper and just ends up looking stupid.
"I could care less" is just careless usage, and does indeed make the speaker sound ignorant.
Over the years I've come to conclude that about half the people who kvetch about "I could care less" (which half may or may not include Chuck but certainly includes my mother...) are so happy to pontificate on how ignorant it is that they really don't want to hear a logical explanation. Same goes for those who kvetch about pronouncing "nuclear" like "nucular".
What's the "logical explanation" for mispronouncing "nuclear"?"
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