Shalom Josh,

Thank you for reaching out to the Kollel with your insightful questions!

In response to your first question, it seems that the practice of the family of Rabban Gamliel placing their coins last in the collection serves as a symbolic gesture that demonstrates respect and honor towards the esteemed leader. Granted, mathematically, it may not hold any discernible difference, since the coins are, indeed, ultimately indistinguishable when mixed with those of other contributors; but the significance of this act lies in its demonstration of reverence and dignity for the community's prominent figure. One might draw an analogy to the occasion where an esteemed community member is invited to place the inaugural brick during the construction of a new Shul.

Regarding the second question, regarding support of an individual Talmid Chacham in comparison to contributing to a yeshiva more broadly, both options possess their unique merits. When one supports a specific Talmid Chacham, like the relationship between Yissachar and Zevulun, it fosters a personal connection and a more direct impact on the scholar's learning. Furthermore, such arrangements often entail explicit stipulations detailing the rewards - both in this world and the next - allocated to each party involved.

Conversely, by supporting a yeshiva as a whole, one can partake in the collective merit generated by the Torah learning of all its students. The virtue of supporting more individuals also might fulfill the Inyan of "ha'Kol Lefi Rov ha'Maaseh" (Avos 3:15) which, according to the Rambam, means that many smaller acts are better than one large act; but possibly not, if ultimately the money is all deposited at once instead separately donated to each indivudal.

R' Moishe Cohen pointed out to me another benefit to donating to a group, namely: to diversify your investment. You may have a greater chance of being Zocheh to provide support to that one-out-of-a-thousand who achieves great levels in Torah. Consider the Yalkut Shimoni on Nach 315:2, which elaborates on the progressive reduction in the number of Torah scholars at each level of learning. From the initial 1000 studying Mikra, only 100 advance to Mishnah, followed by a mere 10 progressing further, and ultimately, a single individual excelling in Gemara.

In the end, because of the virtues associated with each option, until coming across a definitive Psak favoring one over the other, one would be tempted to say that the choice is a matter of personal preference and depends on the specific circumstances.

I hope this helps!

Warmest regards,

Yishai Rasowsky