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I have recently been introduced to formal math and have found that the difficult exercises that are usually found at the ends of chapters really help cement my understanding and intuitive grasp of the material. They usually help me make certain integral realizations. Even when I mull over the material myself and make connections, exercises make me confident that if you wake me up in the middle of the night and ask me a question I'll be able to answer it.

I really enjoy learning Gemara in the most focused and most rigorous manner, which is incredibly mentally and physically demanding (one must exert much energy to truly probe the depths of a sugya). However, I feel that even when I've been able to identify a chakira among Rishonim, get to the bottom of a really difficult tosphot, the area I struggle most in is mastering the art of integrating the nuanced views of all the Rishonim into a coherent picture and being able to directly answer questions that require me to draw from an intuitive and integrated understanding. Even when I've thought deeply about the Rishonim on my own, asked what my Rebbe says are good questions, I don't feel confident in my instantaneous and intuitive grasp of all the nuance.

Therefore, I was wondering if anyone can recommend a book of super high quality exercises in Gemara. That is, not asking what the pshat means, but asking me to go out, read what rishon A, B, and C says, and then prove something with that.

In particular, I am studying Kiddushin, so Kiddushin problems would be really helpful.

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    Sounds like you're looking for my high school Rebbe's extra credit questions on his tests...
    – DonielF
    Apr 14, 2017 at 3:35
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    As an aspirng Statistician I have tried implementing this , but learning Torah cannot be done by using properly when using academic devices IMHO
    – TrustMeI'mARabbi
    Apr 14, 2017 at 3:36
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    To be clear, I'm not advocating for an academic approach to Gemara. I'm merely asking if a sefer exists with excellent, profound, and difficult questions for a student of Gemara to hone his skills
    – theideasmith
    Apr 14, 2017 at 3:56
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    One issue with such a work is that if I ask: what would Rambam say about the following scenario, the book may not assume the same thing you did. These sorts of analyses are much more open to debate.
    – mevaqesh
    Apr 14, 2017 at 4:08
  • That is an extrinsic issue and can easily be solved. The book needs only to exhaustively define its assumptions for each question, leaving nothing ambiguous
    – theideasmith
    Apr 14, 2017 at 4:09

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I would suggest that you learn Shut Rabbi Akiva Eiger, Sefer Chazon Ish, or other such sefarim. When you have learned the author's shailos, try to answer them yourself, based on your knowledge of the sugya. After you have done so, see how the sefer deals with the question.

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  • Thanks so much for this extremely valuable advice. I've spoken with a bunch of people who, like you, have advised me to study particular as opposed to abstract issues, the latter only coming much later in my learning.
    – theideasmith
    May 23, 2017 at 12:54

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