I am drafting a will and intend to designate a large sum of money for my heirs to donate to people who will study Torah in my memory to elevate my soul. (I consulted with an expert who assisted me in drafting wording that meets the halachic requirement for this stipulation to be binding.)

Q: Is it better to give larger amounts of money to fewer people or smaller amounts of money to a greater number?

A: Rambam (Commentary to Avos 3:19) famously writes that it is preferable to give multiple gifts in small amounts rather than one large sum at once. His reasoning is that each time one gives tzedakah he cultivates the trait of generosity. Therefore, it is better to give small amounts multiple times than to give more generously but only once. For this reason, on Purim we give money to at least two people in contrast to mishloach manos where the obligation is to give two gifts to one recipient (Bach and Magen Avraham 965:12). However, this rationale is limited to donations made during one’s lifetime and does not apply to gifts that are given after one has passed on.

Others suggest that giving to many people is advantageous and generates greater reward since one supports more people (Bach, O.C. 695). This rationale applies even in your case and thus it is preferred to give more small gifts than fewer large gifts (Dovev Meisharim 3:144). Another rationale to give to many people is that doing so increases the likelihood that one of the recipients is truly deserving (Yosef Ometz, Tzedakah Umaaser). This rationale also applies in your circumstance (see also Y.D. 257:9 and Tosafos Kiddushin 27a, d.h. Nasun).

Others note that one should carefully consider each situation, since other factors could influence the halachah. For example, the Chofetz Chaim addresses the question of one who receives multiple requests for small loans in addition to a request for a large loan. Although according to the Rambam mentioned above it is preferable to give many small loans, nevertheless, if lending the larger amount will prevent that borrower from becoming destitute, one also fulfills the mitzvah of supporting the poor — thus that loan takes precedence (Ahavas Chessed 1:1:14).

Similarly, Chasam Sofer [6:9] rules that profits generated from money donated to build a wall around a cemetery that cannot be built until permits are obtained should be used to support a single Torah scholar who will study for the benefit of the souls of those buried in that cemetery. He emphasizes that those profits should not be distributed among many people since that will mean that none of the recipients will receive a significant sum.

Accordingly, the money should preferably be distributed in a manner that will allow the recipients to study with greater peace of mind rather than distributing it to many people but not improve their financial situation. Additionally, there are authorities who maintain that Rambam’s approach refers to a situation where each of the gifts will be significant but does not apply when giving to more people will result in each of the recipients receiving a negligible amount (Tzedakah Umishpat 3:[16]; and see also Sefer Chassidim 61).