The little that I know -“I shared this daydream with a menahel, and he angrily told me that he would declare me an enemy of Yiddishkeit. He stated that the yeshiva needs the freedom to pressure the parents for tuition. (I have no idea why.)”
Simple – either he doesn’t have any real poor people in his school, a remote possibility, and he needs to pressure all the fakers; or more likely he doesn’t comprehend the idea of being really poor. I’ve found that a lot of Frum people, whether they are rich or middle-income, don’t really comprehend the Tzoros of a really poor person. They think that it’s like middle-income and at the end of the day, month, year, or whatever, they just don’t have anything left over. They can’t comprehend what it’s like not to have anything in the first place for basic necessities.
And taking Gov. programs doesn’t mean you are poor. It means you meet a certain guideline, but at the end of the day most aren’t really in the poor house. Some will be in the middle-income range and others will be in the upper-income range.