Jewish law is most strict when it comes to accepting charity. "Make your Shabbat like a weekday"--eating less quantitatively and qualitatively--"and do not have need for others [for support]"(Pesachim 113a). The argument that some jobs are too demeaning is addressed by the Talmudic ruling, "Skin carcasses in the marketplace and receive wages, and do not say 'I am a kohen, I am too important a person [for this]!'" (ibid).
In Talmudic times, a Jewish food bank was designed with two types of distribution depots. Those who had only enough food for one week or less were allowed to accept charity from thekupah, the main charity plate. Those whose poverty was so extreme that they did not even have enough money to purchase their next two meals were allowed to collect from the special charity plate known as the tamchui. And those who had food supplies even for just a week were not entitled to utilize food banks.
It is thus somewhat surprising to read, "Do not give him [the impoverished] less that four cups of wine, even if [the money for it comes] from the tamchui" (Pesachim 99b). While drinking wine is a central part of the seder, when all is said and done, it is "only" a rabbinic mitzvah. Would it not be enough to give the poor one cup of wine, or maybe even none at all?
There are times when norms are meant to be broken. For one night a year, on the night we celebrate the forming of our nation, there are no social distinctions. At least for this night, "all men are created equal". Even the poorest of the poor are entitled to feel rich for one night.
The obligation to deplete the charity plates if necessary, also serves as a reminder of the communal obligation to refill those charity plates. Moreover, perhaps the Mishnah is hinting that the mere need for a tamchui is a poor reflection on society. It is great that the poor have somewhere to turn to get food, but tragic that there is a need for such. Society must have as its goal the eradication of poverty, even if in reality, such is unattainable. But if we don't have the goal, there is sure to be a need for more tamchuis. At least on Pesach, the notion of a charity plate must be a foreign one.
The ruling that we are to ensure that the poor have enough wine is the third law of the opening Mishnah of Arvei Pesachim, the tenth and last chapter of the mashechet and the only one that deals with the laws and rituals of the seder. The first law of the Mishnah teaches that one may not eat from mid-afternoon onward on erev Pesach, to ensure that one will eat matzah with a full appetite. While we must feed the poor, those of means can wait to eat. The Mishnah introduces us to the poor with the teaching, "Even the poor in Israel should not eat without reclining"; reclining being the symbol of wealth and freedom.
There is at least one other time that distinctions between rich and poor are eschewed: on Yom Kippur, when "the daughters of Israel would go out with borrowed clothes, so as not to embarrass those who do not have" (Taanit 26b), and dance. When the books of life and death are open, all class distinctions fade away. And it is for this reason that Rabban Gamliel instituted the rule that rich and poor alike are to be buried in simple shrouds (see Moed Katan 27a-b).
It is not possible nor desirable that all should be economically equal. However, ultimately, wealth matters very little. It is our character that is the true legacy that rich and poor alike will pass down to future generations.
 In Talmudic times people ate two meals a day; it was only on Shabbat that three meals were eaten.
 This idea is reflected in the well-known story of the woman who came to Rav Chaim Soloveitchik, asking if she could use milk for the "cups of wine". Rav Chaim gave her a large sum of rubles. When asked as to why he gave her so much more than the cost of wine, Rav Chaim responded that, surely, if she asks if she can drink milk at the seder, she does not have enough money to purchase meat.