Quote: "Flammable and Inflammable mean the same thing?"
Flammable, from Flammare (flame) or Flammula, Latin, can be a small fire or a blazing fire or just a 'flame'.
Inflammable, from inflame and inflame comes from latin too, inflammare, which is to set alight with passion.
So the 'in-' doesn't actually mean what 'in-' usually means and that is to lack. It seems illogical with how we use other words, but there's the etymology of those words, I would
guess that to the latin if something is inflamed, then it is more intense than something that's just flamed, in contradiction to the other usage of that particular prefix.
Ravel vs Unravel has an interesting answer here:
http://www.etymonline.com/index.php?allowed_in_frame=0&search=ravel&searchmode=none
It seems as something unravels ends up getting tangled (or at least where its usage originates), therefore 'ravel' is used to mean 2 contradictory things. The answer: the weavers who confused the two words for us obviously weren't very good at keeping their threads tidy.
Quote: ""I could care less" when what is meant is "I couldn't care less""
I suppose literally speaking: "I could care less" means, "I haven't quite reached my boundaries of not caring, perhaps the version of the phrase was meant to say, "if you carry on I'll just care less and less" and "I couldn't care less" means "I've reached my boundaries of caring" OR simply it might have been, "I couldn't care less" (or 'I could care less') and people have misheard it and it's just evolved that way.
Also, irregardless is now a word, what was once considered a grammatical error (confusion of irrespective and regardless) actually has a dictionary definition, well some still do consider it grammatically incorrect. According to the Oxford Dictionary the usage actually dates back to the 19th Century. And people will still tell others off for using it, so it can be a great way to make a language snob cringe.

Except me, obviously.