Just before I was about to post regarding the Riley/Hiley event, I JUST NOW figured out the correct combination of choices in their route to get the best ending for the club event. So for anyone struggling with this, yes, there is a specific combination of choices you have to make. No there are not hints as to which combination you need.
I feel like if their path ever gets reworked, the correct choices should be made much more clear. I literally had to create a save at the first choice of their path and just try all of the different combinations until I got it. There was no "right" answer. Making the 'correct' choice 'murky' is one thing, but when it's literal guesswork forcing you to reload whenever you get the combination wrong, that's just tedious. Perhaps this was just a limitation of them all being a part of a single route?
That being said, great game so far. Played/finished Part 1 last night and beat it in two cycles. Keep up the great work!