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Answer: There are two approaches to the halachic logic of ma’aser kesafim. Minchat Asher (Devarim 22) discusses whether ma’aser kesafim is an extension of ma’asrot on agricultural produce, or a recommended way of fulfilling one’s tzedaka obligations. The latter seems to be the mainstream approach (see Rambam, Matnot Aniyim 7:5; Shulchan Aruch, Yoreh Deah 249:1).
There are also two main benefits from the mitzva of tzedaka: 1. Making funds available to the needy; 2. Involving the giver in an act of generosity. At times, there is tension between the optimization of these gains. For example, because of #2, it is better to give small amounts of tzedaka many times (Rambam to Avot 3:15), but this can be practically inefficient for organizations (see our attempt at a balanced approach in Living the Halachic Process II, F-3). We do not want to take a stand on the question of efficiency in giving small contributions to individual collectors who already traveled to your shul (their major overhead), and the impact of the difficulty of vetting them. It is, though, both spiritually regrettable and halachically questionable to turn down a poor person without giving him a small donation (see Shulchan Aruch, YD 247:1; Rama, YD 249:4). Your system is therefore understandable, balanced and common.
The short answer to your question is that you may deduct what you give in shul from your ma’aser ledger. Tzedaka is tzedaka, whether it is to an organization or to an individual. Where there is a machloket is whether the tzedaka you give when you have an empty ma’aser account and obligation can later be deducted from future ma’aser kesafim (see Ahavat Chesed II:18:2), and even there we are lenient (Tzedaka U’mishpat 5:11). But it is clear that if you have a ma’aser "pushka" at home and are approached by a collector on the street, you can give him "pocket money," and then reimburse yourself from the pushka. In the same vein, you may write down the contributions and take out money from the tzedaka account or give less next time you replenish your account.
The question is whether you should want to. There is a kabbalistic approach that it is better to give 10% than more than that (Shiyarei Knesset Hagedola, Tur YD 249:1). However, we clearly hold that giving more is laudable (see Shulchan Aruch, YD 249:1). It therefore makes a lot of sense to use the bank account for the 10% and give as you determine appropriate beyond that (if you can afford it). This works well in countering a "problem" with the ma’aser kesafim" system – it "only" requires discipline to calculate and take off the money. However, the actual donations to not include generosity – one gives to Reuven not from his own pocket but by depleting available funds earmarked for the community of the needy. This compromises gain #2 above. If for certain contributions you make you do not seek reimbursement from the ma’aser ledger, those actions (which can be many in certain shuls) is a better fulfillment of the Rambam’s multiple small contributions idea.
Bemare Habazak - Rabbis Questions (652)
Rabbi Daniel Mann
665 - ASK THE RABBI: MENTION OF ROSH CHODESH IN AL HAMICHYA AFTER DARK
666 - Coordinating Ma’aser with Small Donations
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