I believe the idea was to ask “hypothetically, if I found out that this hypothesis was true, how much new information would that give me?”

You’ll have two or more hypotheses, and one of them is the one that would (hypothetically) give you the least amount of new information. The one that would give you the least amount of new information should be considered the “simplest” hypothesis. (assuming a certain definition of “simplest”, and a certain definition of “information”)

I believe the idea was to ask “hypothetically, if I found out that this hypothesis was true, how much new information would that give me?”

You’ll have two or more hypotheses, and one of them is the one that would (hypothetically) give you the least amount of new information. The one that would give you the least amount of new information should be considered the “simplest” hypothesis. (assuming a certain definition of “simplest”, and a certain definition of “information”)