I agree about the fight part (no real game there - it's all up to chance. But I strongly disagree about the e-mails. You have all the information you need for them. I made one mistake there and I don't think the game lets you actually send a mistaken email.
I played the game for the first time with the hint system. It works, the only thing that's counter-intuitive is the fact, that you must go back to the aunt second time to unlock the coffee. Hell, the hints spell out how to achieve a draw in the fashion contest between Ashley and Sophia. Maybe it does the same for the fight, IDK, I used the old walktrough for it and for the dates. The dates are the thing that's the biggest luck IMO - the first point is from the initial compliment and that is hard to figure out without a guide.