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Answer: I urge you to clarify with your congregants that the following rules of engagement are secure for a combination of halachic and practical reasons.
In such a case of only a moderate financial scope, a significant personal one, and technical claims, the sides should assure you they will not allow it to develop an adversarial bent. (Most of) each side’s claim has logic, and they must not be overly disappointed or surprised if they "lose" compared to their expectation. They should view any amount they "lose" not as a shame but as an honor to do the proper thing vis a vis their neighbor. It is no more of a loss than the extra cost of kosher food or of tuition at their children’s schools of choice. Hammering home these ideas is important for at least two reasons. 1) It is true and educational, and this is the right time/setting, as their rabbi, to teach or remind them. 2) If they have an adversarial approach, you are likely to incur resentment from either or both sides for not living up to their expectations. (As dayanim, we are used to that, and it is part of our sacred duty. It is also with people with whom we do not interact in other settings.) As you need to interact with them communally, you do not want to harm relationships. So if they do not have the right attitude, I recommend to refer them to a different framework. (In the shtetl, the rabbi/dayan often had no choice, but our dynamic society offers many options.) Working it out themselves is best but is hard with bad attitudes; mediation or beit din are options.
Next, let us look at your role. Due to a few issues, I suggest not to view or present yourself as an ad-hoc dayan bound to a Choshen Mishpat ruling. First, you have not had sufficient training and practice. Also, it may be very time-consuming to arrive at the correct ruling. Seeking assistance from dayanim minimizes but does not remove the problem.
Also, under normal circumstances, monetary decisions are to be made by a beit din of three, not a lone dayan (Shulchan Aruch, CM 3:1). Even a special expert, who can serve alone, should generally avoid it (ibid. 3, based on Pirkei Avot 4:8). While it may be permitted to do so when the litigants specifically ask for one, it is still problematic (see Shach, CM 3:10). The best solution is to say that your ruling can be either according to halacha, or even a halachic mistake, based on your reasoning.
Bemare Habazak - Rabbis Questions (657)
Rabbi Daniel Mann
267 - Does a Chatan Daven with a Minyan?
268 - A Rabbi’s Approach to Monetary Problem Solving
269 - Husband Accepting Shabbat with his Wife
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All these factors push toward a preference of giving up on the dayanut route in favor of less formal dispute resolution, as was Aharon’s practice, as opposed to Moshe’s (see Sanhedrin 6b). If you can serve as a mediator rather than an arbitrator – great. If they need you to make the decision, then to the extent that halacha guides you – wonderful. However, they should expect a ruling based on peshara, where you bring them to a settlement we wish they would have arrived at alone.
Lessons
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