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Answer: Indeed, the standard ruling is that in most cases, cash gifts are subject to giving mk (see Tzedaka U’mishpat 5:5).
The basic question, whether one maintains a responsibility to take mk on "income" from which he did not take at the appropriate time, arises in different ways. For one who never gave ma’aser, the Shulchan Aruch (Yoreh Deah 249:1, based on Yerushalmi Peah 1:1) prescribes: "The first year, from the principle, subsequently … from what he earned every year." (The Shulchan Aruch discusses a fifth, the maximum rate of giving tzedaka, but the same is true for those who give the "average rate" of mk (Shach ad loc. 2).) Thus, whatever remains in liquid accounts, no matter how he received the funds, would be tithed with the principle, and what was spent is "water under the bridge."
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What happens if one who was already practicing mk failed to tithe some income? The Tashbetz (II:131), focusing on money that had been spent, compares this to one who ate food slated to be given to a kohen or the poor. The gemara (Chulin 130b) says that in such a case, he is not required to pay because there is no specific recipient with rights, and it is only an act of the righteous to do so. Here too, once the money is spent, one need not donate money in its place.
The K’tzot Hachoshen (212:6) views mk differently. He argues that unlike produce to be donated, which applies to specific objects, mk is a matter of accounting how much to give, from any asset. The obligation cannot be "eaten," and there seems no reason for it to disappear over time.
Tzedaka U’mishpat (5:14) cites both opinions without a clear preference. It is difficult to understand the Tashbetz’s logic, as indeed: why should the obligation disappear? Also, when would this occur? Perhaps, one question answers the other.
Poskim discuss making mk calculations at given intervals, which is important according to our ruling that expenses and losses are deducted from profits (Chavot Yair 224). So one needs a cutoff point to know which losses can be deducted from which profits (ibid.). The Noda B’yehuda (II, YD 198) demonstrates that the relevant pasuk and the halacha we cited from the Shulchan Aruch (YD 249:1) hint at a year as a likely mk-calculation period, and the Chavot Yair (ibid.) posits that erev Rosh Hashana is a logical time to do so. Once there is an idea of a periodic accounting, the Tashbetz can view whatever was passed over at that time as relegated to history.
Still, there are several reasons for you to give mk on the past: The K’tzot Hachoshen is likely correct. The Tashbetz says it is praiseworthy to give and you seem interested to do so. If you have not yet spent the money, the Tashbetz might not apply.
As far as estimating amounts, halachic logic would have it that it suffices to give only that which you know you "owe" (Shevet Halevi V:133 disagrees). After all, mk is likely Rabbinic or less and when you accepted upon yourself, you may/should have considered (which is impactful - see Shut Chatam Sofer, YD 231) that you would sometimes forget income and do not want to be liable for what you do not remember. (Many are also more stringent in the system of calculating than may be necessary.) On the other hand, those who can afford to give tzedaka generously are promised reward (see Ta’anit 9a).
P'ninat Mishpat P'ninat Mishpat: Realtor’s Fee on Large Commercial Building – part I
(based on ruling 85031 of the Eretz Hemdah-Gazit Rabbinical Courts)
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(based on ruling 85031 of the Eretz Hemdah-Gazit Rabbinical Courts)
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(based on ruling 83037.1 of the Eretz Hemdah-Gazit Rabbinical Courts)
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Based on Siach Shaul, Pirkei Machshava V’Hadracha p. 690
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