We don't know the first but 2nd is explained very clearly by Lily or DIKs, don't remember which. Before that year, the winner would get a personal stripper for the night since they hired the girls from The Pink Rose before. How far can he go with her would depend on her and him, it's simple. Don't you have at least one girl in mind that would do the same with MC or Derek? There would be a shit ton of options for MC and Ashley for Derek... Maybe Camila for him too... Sadly, we can't know the rest.
But hey, if you play your cards right, you can still get Lily as your personal stripper for your reward hehe
I know you won't see this, but I'm going to respond to it anyway.
The previous year, the reward for getting the most points was a personal stripper from the Pink Rose because the DIKs hired the Pink Rose girls to be at their party. This year, they arranged for the HOTs to be there and although there are certainly some HOTs who could have agreed to be a personal stripper or even more than that for the prize winner, we don't know if that was going to be the case this year.
Also, whether the MC wins or loses the Hell Week points, he got his reward by the fact that he gets to be with 5-6 women in one night, so who needs a personal stripper after that marathon session?
We might also never see or know anything more about this prize because the DIKs have bigger things to worry about right now, what with cleaning up their mansion and the impending fallout from the Cathy pic, so they could easily forget about it.
cheers man,well this time jump you refers,i think about that too and i think the game in two possibilites for the game:
1- As you said the game will have some time jumps,so the game will be the entire college but with time jumps and some text explain what happen in mean time.
2- it will only last one year in game and the a ending explain what happen in the entire college + what happen to the mc and his girl or girls if you plain in maya and josy route.
I think the 2nd one is more likely. This game being about the MC's crazy 1st year at college and how it set his life on a certain path is more likely than jumping into events and moments from different years.