knowing what is an "extra" as opposed to what is essential [really obligated].

There is nothing wrong with trying to be as strict as possible in keeping the holy Torah. The issue is that without having gone through Shas at least once, one does not have any means of knowing what is an "extra" as opposed to what is essential [really obligated]. While at the Mir and Shar Yashuv in NY this distinction did not make much difference to me because I was trying in fact to keep everything, including when there are differences of opinion I would go after the stricter opinion. This is a great thing to do.

However after I got to Israel and was learning the Le.M of Rav Nahman, I noted that he mentioned II:44 and II:86 that to serve God, one does not need any extra restrictions. And later when my world started crumbling around me (note 1), I found this distinction to be of great importance--i.e., to know what is really obligated and what is just an extra.

[I would think this to be obvious, but a few days ago I was talking with a friend on the street and this issue came up. After all I had suggested to him the importance of learning Torah, and so he now goes often to a place where there people are in fact very focused on learning Torah. But he also noticed this same aspect of things: to strive to be extra strict. So he was wondering why and in what ways is my path different, even though I am in total agreement with the importance of learning Torah and striving to keep every detail to the last atom and molecule. 

[But to know what the Torah really requires, it is also mostly enough to learn the Mishna with the Rav of Bartenura who explains things well and also gives the actual way the law is decided. After doing that a few times, then to get through Shas.]  

(note 1) It is hard to keep everything when you have no place to sleep. No place to learn. All your "friends turn out to be fair weather friends.

Ketuboth page19.כתובות דף י''ט Rav Shach brings this subject in Laws of Loans perek 2 halacha 6.

 I have been thinking about a גמרא brought in כתובות דף י''ט. There ר' נתן said if you have a case where לוי owes ראובן 100 and ראובן owes שמעון 100, you take from לוי and give to שמעון. If ראובן has a document showing that לוי owes him and לוי says it is paid already and ראובן agrees, we pay no attention to them since they might have conspired. What has been bothering me about this is that the property of לוי is anyway going to ראובן and from there to שמעון. So mainly what IS going on is the middle step. But then even more so you have the ר''ן there that asks  this: Why not just collect the document from ראובן. And he answers שטרות לאו בני גוביינא נינהוא שאין גופם ממון.  Documents can not be taken as payment for a loan because they are not money in themselves. The general case when someone does not pay back a loan, the court can go and get land or movable property. What was bothering me was this question and answer of the ר''ן [רבינו ניסים]. Not that I have an actual question, just a sort of question in which I am wondering what is going on? Apparently in the first case we already know that לוי owes money to ראובן. So how do we know that? By the document! So what is collecting the document going to add anything to the situation? How would it help שמעון any more than we already are helping him recover the debt?

The ר''ן here asks why not collect the document showing that לוי owes money to ראובן. I wondered why this would make any difference if we already know that he owes money. Answer: because a loan with a document is more powerful than a loan without. It gets from property that was sold after the loan was made. 

The thing that makes the question of the Ran powerful is that if you have a case of a loan which is verbal, not with a document, the lender is believed if he says I paid it.  However I should add that this is not the normal case of a verbal loan since here the lender would not be believed because of the possibility that he is conspiring with the middle borrower to cheat Shimon.   

I have thought of a way of explaining the power of the question of the ר''ן.  It seems like this: The middle person, ראובן, has a document that לוי owes him money. And שמעון has a document showing that ראובן owes him money. But  ראובן has no money, nor any property that he sold after he borrowed.  But he has a document showing that Levi owes him money. So none of the property of לוי would come to  ראובן directly if not for the law of ר' נתן in כתובות י''ט. The point of the ר''ן is that perhaps the document of  ראובן ought to be given to שמעון in which case he would have a stronger claim on לוי. As it is is now, if לוי says the document has been paid and  ראובן agrees, we do not believe them because of a doubt. Maybe they are conspiring against שמעון. But if שמעון would have the document itself  that shows לוי owes him  money then from the basic law of loans לוי would not be believed because in the case of a loan with a document, the plea "I paid already" is not believed. 

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 I have been thinking about a gemara brought in Ketuboth page19. There R. Natan said if you have a case where Levi owes Reuben 100 and Reuben owes Simon 100, you take from Levi and give to Simon. If Reuben has a document showing that Levi owes him and Levi says it is paid already and Reuben agrees, we pay no attention to them since they might have conspired. What has been bothering me about this is that the property of Levi is anyway going to Reuben and from there to Simon. So mainly what i going on is the middle step. But then even more so you have the Ran there that asks  this: Why not just collect the document from Reuben. And he answers שטרות לאו בני גוביינא נינהוא שאין גופם ממון.  Documents can not be taken as payment for a loan because they are not money in themselves. [The general case when someone does not pay back a loan, the court can go and get land or movable property]

What was bothering me at the beach the whole day was this question and answer of the Ran [Rabbainu Nisim]. Not that I have an actual question, just a sort of question in which I am wondering what is going on? Apparently in the first case we already know that Levi owes money to Reuben. So how do we know that? By the document! So what is collecting the document going to add anything to the situation? [How would it help Simon any more than we already are helping him recover the debt?]

The ר''ן here asks why not collect the document showing that לוי owes money to ראובן. I wondered why this would make any difference if we already know that he owes money. Answer: because a loan with a document is more powerful than a loan without. It gets from property that was sold after the loan was made.

The thing that makes the question of the ר''ן powerful is that if you have a case of a loan which is verbal, not with a document, the lender is believed if he says, "I paid it."  However I should add that this is not the normal case of a verbal loan, since here the lender would not be believed because of the possibility that he is conspiring with the middle borrower to cheat שמעון.   

I have thought of a way of explaining the power of the question of the Ran.  It seems like this: The middle person Reuven has a document that Levi owes him money. And Shimon has a document showing that Reuven owes him money. But Reuven ha no money nor any property that he sold after he borrowed.  But he has a document showing that Levi owes him money. So none of the property of Levi would come to Reuven directly if not for the law of R. Natan in Ketuboth 19. The point of the Ran is that perhaps the document of Reuven ought to be given to Shimon in which case he would have a stronger claim on Levi. As it is is now, if Levi says the document has been paid and Reuven agrees , we do not believe them because of a doubt. Maybe they are conspiring against Shimon. But if Shimon would have the document itself  that shows Levi owes him  money then from the basic law of loans Levi would not be believed because in the case of a loan with a document, the plea "I paid already" is not believed. 

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חשבתי על גמרא שהובאה בכתובות דף י''ט. שם ר' נתן אמר אם יש לך מקרה שבו לוי חייב לראובן 100 וראובן חייב לשמעון 100, אתה לוקח מלוי ונותן לשמעון. אם לראובן יש מסמך שמראה שלוי חייב לו ולוי אומר שזה כבר שולם וראובן מסכים, אנחנו לא שמים לב אליהם כי ייתכן שהם קשרו קשר. מה שהפריע לי בזה הוא שהרכוש של לוי ממילא הולך לראובן ומשם לשמעון. אז בעיקר מה שקורה הוא הצעד האמצעי. אבל אז עוד יותר יש לך את הר''ן שם ששואל את זה: למה לא פשוט לאסוף את המסמך מראובן. והוא עונה שטרות לאו בני גוביינא נינהוא שאין גופם ממון. לא ניתן לקחת מסמכים כתשלום עבור הלוואה כי הם אינם כסף בפני עצמם. במקרה הכללי כאשר מישהו לא מחזיר הלוואה, בית המשפט יכול ללכת לקבל קרקע או מטלטלין. מה שהפריע לי זו השאלה והתשובה של הר''ן [רבינו ניסים]. לא שיש לי שאלה ממשית, רק מעין שאלה שבה אני תוהה מה קורה? כנראה שבמקרה הראשון אנחנו כבר יודעים שלוי חייב כסף לראובן. אז איך אנחנו יודעים את זה? לפי המסמך! אז מה איסוף המסמך יוסיף משהו למצב? איך זה יעזור לשמעון יותר ממה שאנחנו כבר עוזרים לו לגבות את החוב?

הר''ן כאן שואל למה לא לאסוף את המסמך שמראה שלוי חייב כסף לראובן. תהיתי למה זה ישנה משהו אם אנחנו כבר יודעים שהוא חייב כסף. תשובה: כי הלוואה עם  מסמך חזקה יותר מהלוואה בלי. זה מגיע מנכס שנמכר לאחר מתן ההלוואה (משועבדים). הדבר שעושה את שאלת הר''ן חזקה הוא שאם יש לך מקרה של הלוואה שהיא מילולית (מלווה על פה), לא עם מסמך, מאמינים למלווה אם הוא אומר "שילמתי". עם זאת אוסיף שאין זה המקרה הרגיל של הלוואה מילולית, שכן כאן לא יאמינו למלווה בגלל האפשרות שהוא קושר קשר עם הלווה האמצעי לרמות את שמעון. חשבתי על דרך להסביר את כוחה של שאלת הר''ן. זה נראה כך: לאדם האמצעי ראובן יש מסמך שלוי חייב לו כסף. ולשמעון יש מסמך שמראה שראובן חייב לו כסף. אבל לראובן אין כסף או רכוש שהוא מכר אחרי שהוא לווה. אבל יש לו מסמך שמראה שלוי חייב לו כסף. אז ששום דבר מרכושו של לוי לא היה מגיע ישירות לראובן אלמלא דין ר' נתן בכתובות י''ט. הנקודה של הר''ן היא שאולי צריך למסור את המסמך של ראובן לשמעון שבמקרה כזה תהיה לו תביעה יותר חזקה על לוי. כפי שזה עכשיו, אם לוי אומר שהמסמך שולם וראובן מסכים, אנחנו לא מאמינים להם בגלל ספק. אולי הם קושרים קשר נגד שמעון. אבל אם לשמעון היה המסמך עצמו שמראה שלוי חייב לו כסף אז מחוק ההלוואות היסוד לוי לא היה נאמן כי במקרה של הלוואה עם מסמך, לא מאמינים לטענת "כבר שילמתי".