My good. Death is part of life. AL was so dramatic and I never played it because the MC was forced to make a decision. It was up to him if which girl he wanted to save. The dramatic thing was the decision.
If someone has a misfortune or dies of natural causes, the MC can't control that, so it would be dramatic, but it would be out of his hands.
For example, what if the MC learned that his mother had been in a coma for 19 years and he was sitting outside her room? Then the $5,000 would not have been an inheritance, but just a covert support. The facial expression could then be interpreted differently, as the MC might think with horror that Neil has lied to him for 19 years.
In EP2's Steve Major Choice 3, we learn that Steve's father is divorcing his mother and that Steve is living with his mother. The MC said that he would do the same.
Read for yourself what book Jill is reading.