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This is only a partial answer. I have heard from Rabbi Moshe Sternbuch, (formerly in South Africa where he was my family's Rav, now Raavad of the Edah Hachareidis, Jerusalem), that a Baal teshuva does NOT wear tefilin on Chol Hamoed as this is lechumrah. One only wears tefilin, if one has an existing family tradition to do so.



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