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To what lengths must one go to fulfill a positive commandment, or avoid transgressing a negative one?

Obviously, with few exceptions, one must not go so far as to die in order to fulfill a commandment. However, short of that, how far must one go? Must (may) one make oneself sick in order to do a mitzvah? Must one spend so much money in doing a mitzvah that one is reduced to begging thereafter? Must one suffer even the most extreme emotional toll in order to perform a mitzvah?

Does any of this depend on the nature of the mitzvah, or vary for specific (individual) mitzvot?

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"Rama, Orach Chaim 656:1, rules that one must spend up to one-fifth of his assets on order to fulfill a positive mitzvah and his entire fortune in order not to violate a negative commandment." (source) As for negative commandments that are violated by passivity--such as the commandment that you may not allow someone else to die--there is dispute about whether they are considered "positive" or "negative" commandments for the purposes of this question. R. Yair Bachrach, in Chavot Yair no. 139, considers this example a positive commandment, which one must spend up to one-fifth of his assets to fulfill, whereas Rivash (no. 387) considers it a negative commandment for which one must spend one's entire fortune.

As for illness: a choleh or sick person is considered exempt from some mitzvot, notably fasting, but Rabbinical opinions seem to vary substantially as to the full extent of a sick person's exemptions from mitzvot. Some opinions are discussed here. Very generally, it seems that a sick person is often exempt from positive commandments but rarely negative ones. (CYLOR if it applies to you, of course...)

The question of whether one should make himself ill--including, perhaps, emotional illness--in order to fulfill a commandment is another question of debate, but at least one authority suggests that "Since one is not required to spend more than a fifth of his assets for a mitzvas aseh then certainly one is not required to make himself sick." Whether it would be permissible to do so (i.e., to make oneself sick in order to perform a mitzvah) is still unclear to me.

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"Since one is not required to spend... one is not required to make himself sick." This is also the ruling of R' Moshe Feinstein (Igros Moshe OC vol. 1, 172). As far as whether it is permitted, see Y'rushalmi P'sachim (10:1) where R' Yona and R' Yuda drank the four cups of wine at the seder even though they suffered headaches for months afterwards as a result: רבי יונה כדעתיה דרבי יונה שתי ארבעתי כסוי דלילי פסחא וחזיק רישיה עד עצרתה רבי יודה בי רבי אלעי שתי ארבעתי כסוי דלילי פיסחא וחזיק רישיה עד חגא. (Though perhaps one can argue about whether headaches are considered an illness). –  Fred Mar 19 '13 at 16:53
    
Would someone be so kind as to translate the Hebrew quote for me? –  SAH Oct 4 '13 at 21:26
    
"Rabbi Yonah follows his own opinion [that one may drink mevushal (cooked) wine for the four cups], for Rabbi Yonah drank the four cups on the night of Passover and suffered headaches until Shavuos. Rabbi Yudah [did likewise] and suffered headaches until Sukkos." I just looked up the Korban HaEida commentary on this, which explains that Rabbi Yonah, after experiencing persistent headaches, subsequently permitted drinking mevushal wine (which is generally considered inferior to non-mevushal wine) for the four cups, since it is less likely to harm one's health. –  Fred Oct 7 '13 at 2:12
    
@Fred How does KH interpret R Yudah's story? He also permitted such wine after extensive headaches? –  Double AA 10 hours ago
    
@DoubleAA Most likely, the KH would say that R' Yehuda bar Il'ai reacted to his unpleasant experience in a similar manner. As the Yerushalmi mentions, R' Yudah permitted diluted wine, while R' Yonah permitted m'vushal. A discussion on the halachic differences between mazug and m'vushal is interesting in and of itself, but perhaps one approach to the difference between the earlier ruling of R' Yudah permitting mazug and the later ruling of R' Yonah permitting m'vushal is that m'vushal may have simply been an uncommon form of wine back in R' Yudah's time (see Rosh Avoda Zara 2:13). –  Fred 50 mins ago
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