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My understanding is that " 百姓 " is a very impolite way to refer to modern-day traditional Japanese farmers. A good translation might be " country bumpkin ".

As best I can remember:
I learned that word while relaxing with friends at an 居酒屋{いざかや} in Tokyo. Subsequent to that, I tried using it in daily conversations with not very close friends. Each time, I was cautioned about saying " 百姓 ". Those who refer to farmers as " 百姓 " imply that they, themselves, are cultured and refined, while the " 百姓 " lead uneducated, unrefined, bumpkin-ish lifestyles.

  1. Is my recollection of meaning and usage correct?
  2. In what type of settings would a non-native Japanese speaker be able to say " 百姓 " and not be judged as an elitist jerk? In fact, I'd hope to be judged as being someone who knows clever slang.
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1.Is my recollection of meaning and usage correct?

Yes, it is correct and that is because 「[百姓]{ひゃくしょう}」 is closer to "peasant" than to "farmer" in feeling.

2.In what type of settings would a non-native Japanese speaker be able to say " 百姓 " and not be judged as an elitist jerk? In fact, I'd hope to be judged as being someone who knows clever slang.

Whether you are a Japanese-learner or native speaker, there are basically no situations where you can call a farmer a 百姓. The only exception would be when a farmer calls himself a 百姓, which happens quite often.

We have the term 「お百姓さん」, which sounds more "correct" than the plain 「百姓」 but it still would not be used much in public by the more careful speakers -- in particular, by the media. In private conversations, though, it is heard fairly often.

The safest word choices have been given by @Unknown in the comment section above.

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