What are the bounds and limits for helping another person out, and to what extent is there a legal halachic obligation? Our Gemara on amud beis describes a situation where a man is not obligated personally to perform chalitzah, as according to his account he is not bound by yibum and she was not able to furnish objective proof as to her status. However, the woman, according to her subjective account, is bound by her own admission. That is, the Beis Din does not believe her insofar as to impose this obligation on the man, but since she believes it is true by her own admission, she is still legally bound. In such a case, the Gemara states, that “request of him to perform ḥalitza with her.” It is a request, but not an obligation.
Tosafos picks up on this and asks why don’t we force him to do so since it causes him no loss? Tosafos answers that since it is humiliating to be spit at during the chalitzah process, he does have the right to refuse to endure it, since the objective facts have not proven him to be bound by yibum.
The Chochmas Shelomo elaborates on Tosafos’ reasoning. If he would not have to suffer any embarrassment, Beis Din indeed would force him to do chalitzah because of the principle of, kofin al midas sodom, we force people to allow others to gain if they do not incur any loss.
This Chochmas Shelomo is a chiddush because classically we invoke the Middas Sodom principle only in regard to passively allowing someone to benefit from your possessions, if it incurs no loss to you. Examples include using a person’s property or airspace when it does not disturb them significantly (see Shulkhan Arukh CM 153:8 and 154:3). Here, we are pushing the obligation up one notch, as the expectation is upon the person to do an action, though relatively innocuous (in Tosafos’ initial assessment), because of the great benefit it brings to the other. We are applying a relative loss benefit ratio to the situation.
So far our discussion is about what one is obligated and even can be forced to do. What about matters that it is right to do, but not an absolute obligation? And, are there certain favors that are even wrong to do, such as if they enable dysfunction?
In terms of not being obligated but still being the right thing to do, let us consider this example from Gemara Bava Metzia (30a):
The mishna teaches: If a person found a sack or a basket or any other item that it is not his typical manner to take and carry because it is beneath his dignity, he shall not take it. The Gemara asks: From where are these matters derived? It is as the Sages taught in a baraita: It is stated with regard to the return of a lost item: “You shall not see your brother’s ox or his sheep wandering and disregard them; you shall return them to your brother” (Deuteronomy 22:1). The tanna explains that the phrase “and disregard them” means that there are occasions in which you may disregard lost items and there are occasions in which you may not disregard them.
How so; under what circumstances may one disregard a lost item? One may do so in a case …where he was an elderly person and it is not in keeping with his dignity to tend to the item, or where the value of his labor was greater than the value of the lost item of the other person, i.e., if the finder was to return the item, reimbursing him for his lost wages would cost more than the value of the item; therefore, it is stated: “And disregard them.”
I think we can extrapolate from this halakha, that in matters of chessed between man and fellow man, if the action is something that you yourself would not prefer to do for yourself, then you are not obligated to do so for others. Such as, if someone asks you for a ride across town, which takes you 10 minutes out of your way, you can evaluate it as follows: If the benefit to that person is something I would do for myself, if I were him, then I should help him as well.
One should be careful in this evaluation, as subjective difficulty and benefit must be evaluated. A healthy person might have no problem walking a half mile, while a less hardy person may need the ride more.
Perhaps a better scale to evaluate this matter, is if overall, there is more benefit than loss, or not. For example, if in giving a person a ride across town you lose 5 minutes but save the person 10 minutes, there is an overall gain and lessening of human suffering. However, if you save the person 10 minutes, but the traffic back costs you 20 minutes, maybe HE should do YOU the favor by walking!
As for the last category, where helping someone may enable dysfunction and therefore should not be done. Kli Yakkar (Shemos 23:5) makes the case that one is not obligated to help someone who makes no effort to help himself. The verse describes a situation, where you happen upon someone whose donkey has fallen under a burden you are obligated to assist him, even if it is someone whom you despise. Nevertheless, the language used is “help with him"
“If you happen upon the donkey of your enemy fallen under its load, and you hold back from helping him, you must surely work with him to assist him with unloading the donkey.”
Kliy Yakkar explains:
“The phrase ‘with him’ informs us he must specifically want to work with you. Only then are you obligated to help him. However, in a situation where he sits back and says, ‘Since you are obligated to help me, you are solely responsible’, that is why the verse states ‘and you hold back from helping him’. The implication is that when it is helping him only, and him not working along with you, then it is is indeed permitted to hold back assistance.
From here we see a rebuke to some of the impoverished people of our nation who burden the community and refuse to take upon themselves any employment despite having the ability to work or generate income for themselves and their families. Moreover, they raise a hue and cry if we do not provide them with their needed supports. This is not in accordance with Hashem’s command, as we only are to provide assistance along with their own efforts. The destitute person must make every effort to support himself, and then if he cannot fully succeed, every Jew must help him and support him with no limits."
Kli Yakkar’s position is apparently that there is no obligation of chessed or tzedakah when the recipient is lazy or otherwise not showing adequate initiative to help himself.
Translations Courtesy of Sefaria, except when, sometimes, I disagree with the translation 
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