The needless cruel part is not paying back the money, but explicitly linking it to then getting out from having dinner with her parents once a week, and by extension assuming that Rory will rejoice at being released of that burden as well.

Exactly. One of the central aspects of Lorelai's character is that she's basically a saint _except_ when dealing with her parents (and occassionally with Jess). This particular episode with the $75000 struck me as one of the most petty and needlessly cruel things that Lorelai ever does to her parents, but totally in…