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> Here it's often seen as a little sarcastic or teasing as there's a tiny culture implication that it means they didn't prepare enough.

I have always thought the same thing about "Good for you" which I think would commonly be translated as "Schön für dich". You cannot possibly say that without sounding sarcastic.

Regarding "Viel Glück", I usually use "Viel Erfolg" when I'm being sincere.

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"Good for you" I think sounds ridiculously sarcastic in British English, fwiw.

Even in American English you would have to be incredibly chipper and sincere for it not to sound sarcastic.

Yes! That's a great example of words that have different meaning conveying a similar context. ("Viel Erfolg" meaning more like "Lots of success."/"I wish you success"). Even that though I feel has a bit of different subtext. Honestly that's the hardest thing about learning another language. Even after 10 years here I often say something which in meaning is exactly correct but still fails to convey what I wish due to some cultural subtext that I wasn't aware of.

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