Freedom of Choice, The Impetus for Creation

 The Gemara in Menachos says as follows:

כדדרש ר' יהודה בר ר' אילעאי אלו שני עולמות שברא הקב''ה אחד בה''י ואחד ביו''ד ואיני יודע אם העולם הבא ביו''ד והעולם הזה בה''י אם העולם הזה ביו''ד והעולם הבא בה''י כשהוא אומר {בראשית ב-ד} אלה תולדות השמים והארץ בהבראם אל תקרי בהבראם אלא בה''י בראם [הוי אומר העולם הזה בה''י והעולם הבא ביו''ד] ומפני מה נברא העולם הזה בה''י מפני שדומה לאכסדרה שכל הרוצה לצאת יצא

Rashi says on  כל הרוצה לצאת יצא:

שכל הרוצה לצאת. ממנו לתרבות רעה יוצא

This world was created in such a fashion that anyone can rebel and go his own way against God. This sounds reasonable on the surface. However, the Gemara is obviously saying much more than that. The Gemara says מפני מה נברא העולם הזה בה''י. The Gemara doesn't say that there is free will that anybody can do what they want. The Gemara says that the world was created with the letter ה. Meaning that it is not an one of the aspects of the world or one of the dimensions of existance but rather the how, why, what, and where the world was created. This concepts is the most inherent part of creation to the extent that the letter  ה which is mostly defined by the ability to escape was the one letter chosen to create the world. 

The Gemara is saying that the MOST fundamental concept of creation the raison' d'etre for creation was to create a space that כל הרוצה לצאת יצא. It would not be possible to have a world without free will. The founding fathers of the United States got it right when they stated that the two most fundamental rights are life and liberty. Liberty is as fundamental as life itself. Life without liberty is not life. An animal has life without liberty. 

We, as a society, are obligated to follow God's ways. Any law that society creates that impedes another's liberty is a fundamental sin. Understandably a society cannot function without basic laws in place, mostly laws that don't allow people to impede other's liberties. However, the perspective must be that  all man made laws imposing on others usually by government are necessary evils. The more we allow for free will the more Godly we are as a society. Hence historically the most free societies were the most Godly ones and the least free societies have always been the least Godly ones. (not religious but Godly)

Every law, every imposition, every mandate, decree, and ordinance fostered on others moves us, as a society, further from Godliness. To serve God the way he wants us to serve him we must allow for absolute freedom of choice just as He left us. 

Paskening Din (Monetary Issues) Vs. Paskening Issur

 The Gemara in Bechoros (49A, Niddah 64A, Eiruvin 93B) says that when Rav argues with Shmuel we pasken like Rav with regard to Issur. The Ros'h in Perek Hazahav says that in Dinim we pasken like Shmuel. 

The Rosh in Bava Kama (4th Perek Siman Daled) explains simply that Shmuel was a Dayan and therefore more proficient in Dinei Mamonos while Rav was a Posek and therefore more proficient in Hilchos Issur. 

The Chavas Yair (Siman 94) says a very interesting chiddush. The Chavas Yair posits that Rav, who is Tanna Upalig was a buki (expert) in Mishnayos and Braysos and had a very wide breadth of knowledge to the extent that he had the authority to argue on Tannaim. This breadth of knowledge was so great that when he argued with Shumel we always paken like him (Rav). Shmuel, on the other hand, as it is well know was  an expert doctor and moreover, as he himself stated, very knowledgeable in Astronomy and other sciences. Shmuel, states the Chavas Yair, was not as big of an expert in Mishna, Braisa, Tosefta, as Rav but rather had a much more well rounded education. Therefore, when it came to Halacha we pasken like Rav. However, regarding Dinei Mamonos (Monetary issues) having a sharp mind and the ability to analyze a situation allowed Shmuel to be better equiped to pasken Dinim. 

In short, the Chavas Yair seems to be saying that for Issur for Heter you need to be a "Sinai" and the bigger "Sinai" one is the more we can rely on him for psak. However, for Dinim you need to be an "Oker Harim" (one who keen analytical abilities) and Shmuel, although he didn't know as much as Rav, had better analysis tools. The Chavas Yair also adds that the fact that Shmuel had a proficiency in these other disciplines gave him an edge in paskening Din. 

There is much more "Svara" in Choshen Mishpat than there is in the rest of Shulchan Aruch. Halachic knowledge without keen Svara can only get one so far regarding Choshen Mishpat laws.