g_a_w, can you please cite a source in halacha that states that a Jew must do without a certain amount of heat and Shabbos clothing rather than accept tzeddaka? And that someone who can afford to give, shouldn’t give to such a person? My impression was klal yisroel was always more giving (and went “above and beyind” the letter — although in this case it is bare minimums we are discussing.)
You wrote: “we are not discussing those who had a job which would have paid the 50K in tuition in the first place”. I don’t see how this would be any different from someone who was poor all his life, and couldn’t afford it from the onset.
And since you are moida that you are chayiv to pay for them, that is the only concern of yours. Whether he is chayiv to give them up is between him and G-d. Between you and G-d, you are chayiv to assist.