(12) If a fellow Hebrew, man or woman, is sold to you, he shall serve you six years, and in the seventh year you shall set him free. (13) When you set him free, do not let him go empty-handed: (14) Adorn him liberally out of the flock, threshing floor, and vat, with which the LORD your God has blessed you. (15) Bear in mind that you were slaves in the land of Egypt and the LORD your God redeemed you; therefore I enjoin this commandment upon you today.

הענק תעניק — denoting an ornament worn high up on the body which thus easily visible to the eye, i.e., something that patently shows you were kind to him. Some explain it to mean you literally place the gift on his neck.

(2) One might think the obligation is limited to these things, therefore it states “that which the Lord blessed thee” namely, with everything that Hashem blessed you with. Why mention these specifically? Just as these enjoy “blessing”, (i.e. propagating) so, too, you should give things that are a “blessing,” thus excluding mules, (which are sterile) (Sifrei Devarim 119:3). — Our Rabbis have derived in Kiddushin 17a by analogous expressions (גז"ש) what quantities one must give him of all the different kinds here mentioned.

(2) The root of the commandment is in order to acquire for our souls virtuous, dear and beautiful traits; for with a dear and virtuous soul, we will merit the good - and the good God wants to do good for His people. And our glory and splendor is that we show mercy to those we employ and to give them from our assets as a rite of kindness - above and beyond the negotiated wage. This is intuitive and does not require a lengthy discourse....(4) ...Nonetheless, even nowadays when there is no Eved Ivri extant, 'the wise man listens and adds insight' - such that if you employ a Jew, whether he works for you for a long time or even a short time, when he leaves your employ you should endow him with that which God blessed you.

"You shall set aside a tenth..." so that you do not lose, tithe and you will be enriched. Hashem said, tithe what is mine and I will enrich [tenfold] what is yours. "[Tithe] from all [the yield of your plantings...]," Rav Abba bar Kahane said this alludes to the merchants and the sea travelers [who do not earn from the produce of the land] that they should set aside one tenth for those who delve in Torah.

We find in the Sifri: "You shall set aside a tenth part of all the yield of your sowing that is brought from the field every year" I might have concluded that one is only obligated to tithe the crops from planting, but from where do I know that the tithe obligation encompasses earnings from interest, merchandise and all other profits? The text adds "all" - to teach you that it includes interest, merchandise and all other types of profits.

Rabbi Ile’a said: In Usha they instituted a cap on charity so that one should not dispense more than one-fifth. As the baraita taught: lest he render himself destitute and need the help of other people. And an incident occurred involving an individual who sought to donate more than one-fifth of his property as charity, and his friend did not let him. And who was this friend? Rabbi Yeshevav. And some say Rabbi Yeshevav was donor and the friend who would not let him was Rabbi Akiva. Rav Naḥman said, and some say it was Rav Aḥa bar Ya’akov: What is the verse “And of all that You shall give me, I will surely give tenth n tenth [aser a’asrenu] to You” (Genesis 28:22) [two tenths = one fifth]

The amount of charity one should give is as follows: if one can but afford, let him give as much as is needed. Under ordinary circumstances, a fifth of one's property is most laudable. To give one-tenth is the average disposition. But to give less than one-tenth is miserly. When the Rabbis said a "fifth" they meant a fifth of the property the first year only and a fifth of the profits in succeeding years. RMI.—But a man should not squander more than one-fifth to charity, so that he might not himself become a public charge.This refers only to his lifetime. Of course, at the time of death one may leave for charity as much as he pleases. But one should not expend the tithe moneys to fund a mere mitvah (e.g., lighting for the shul) but it should be for the poor.

The Maharshal and Drisha report a responsa of R. Meir of Rothenberg that one may use Maaser money to fund any mitzvah presented (e.g., a circumcision or a hachnasas kalla, etc.); or to buy religious books for either self study or to loan to others to study; or any other mitzvah one needed funds to afford. Similarly, one could dispense Maaser money to support one's grown children (who are beyond the age of mandatory child support), or an impoverished parent. The Taz writes that one may not use the Maaser funds to pay [communal] taxes [since that is a essentially a financial obligation]...