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He's a senior in high school and a very smart, analytical fellow though he lacks some basic textual skills because he's in public school. Going for gap year yeshiva next year and they said he should get basic fluency reading/understanding Gemara.

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B"H

Usually children begin learning Gemara with the chapter אלו מציאות, in Bava Metzia.

While it is actually quite complex, as is any chapter in Gemara when learned with more depth and concentration, it is still considered one of the standard "simple" chapters that kids start learning Gemara with. Another beginner chapter is הכונס צאן, in Bava Kamma, as well.

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    Welcome to MiYodeya and thanks for this first answer. Since MY is different from other sites you might be used to, see here for a guide which might help understand the site. Great to have you learn with us! – mbloch Mar 19 '24 at 03:58
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    A good reason to choose אלו מציאות is that it has many repetitions of similar phrases, which allows the student to gain momentum in their reading. It's difficult for new students when they need to ask about every word in a sentence, so when there are sentences made up of phrases that they learned in the beginning of the lesson, they can actually focus on learning the style of logic and feel like they are accomplishing something, instead of getting caught on the language barrier. – Ethan Leonard Mar 19 '24 at 10:44