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Putting in my two cents: I'm from Texas and "that's too bad" isn't a dirty phrase to me, and we say it at home. I admit, it has it's uses (ie. "How are you today?" "Ah, not so good" "Oh? That's too bad :/") and that in most cases there is a better phrase. But you can tell the Koreans don't mean it sarcastically when they say it.

The words themselves shouldn't be so reactive if they mean it in the right way. These are just kids learning a foreign language. But i would agree that trying to teach them "I'm sorry (to hear that)." as well is probably a good option.

What's the big deal with the material in the books?  You are not paid to question the wisdom of the textbook overlords.  You must teach them as much archaic language as possible.

Seriously though, the goal for NETs should be to facilitate successful, not perfect, communication.   That's too bad is easier to remember because it has simple vocabulary and is easy to pronounce.   So, grind your teeth and quit complaining.

You're banning the use of a safety phrase among beginner learners because it personally annoys you?
 
I'm going to have to agree with the 'there's nothing wrong with it' people... it's one phrase that's used accurately in Korea.. unlike 'take a rest' or 'I will ride you'. 

I'd only ever heard it used in a sarcastic manner before coming to Korea. "I'm sorry to hear that." is probably a better alternative and isn't any more complex.

You're going to have to teach them anyway though. I mean, either you teach them "That's too bad." or you let them fail that part of the Office of Education-set test. Now that's too bad.

That's correct, only sarcastically. Actually, I think I might have heard it used non-sarcastically in Japan too, but that's another EFL environment.

I'm from Australia.

I agree with the notion to ban this phrase for the exact same reasons.  From my understanding, many of the awkward phrases in these textbooks are simply the closest translation to Korean the writers could find.   This of course means that there is an obvious lack of authenticity (which is a shame really since there are over 37,000 foreign teachers they could have check these books before they publish them).

I really think with this phrase it depends on how its said, but since most Korean students speak in complete monotone and have no intonation, it always sounds like an unsympathetic robot child.