So far, the game has been played in real time. So he'll have to change from that, to have any chance of getting through the full 8 week period. Because at the moment, he's spending multiple updates on each game day. So either switch to less content per day or as you suggest jump forward a week, every so often.
And I think he really needs to limit Phil's content appearances to once a day, because otherwise he's going to have to recycle a lot of his content, because there's a severe limit to what you can do, in that location, with basically only 2 women and a bunch of men. Because even if Phil manages to have sex with the Air Hostess, most of the time you wouldn't expect her to be in Alaska, or anywhere close to the remote area that Phil is working in. So short of the occasional visit to an Alaskan city with an airport, what chance would Phil have, of meeting up with her, or anyone else. That means his only realistic options through most of the game are the two women, plus Gareth if he's bisexual, and they can only ever have sex in one or two locations.
We already know that Phil can have sex with Gareth and Maria whenever he wants, since both of them are really promiscuous. So there's no room there for any gradual development of any sex content. And based on her slutty appearance and behaviour, I'm guessing the Air Hostess will be exactly the same. So that only leaves the boss lady for Phil to potentially have to put some effort, into bedding her. So what we going to have, another party in somebody else's bedroom, so he gets another chance to seduce her, followed by exactly the same threesome scene with Gareth and Maria (if Phil is bisexual)?
I honestly don't why he decided to include Phil, because he's put him in such a ridiculously limited location, that you can't realistically make his side of the storyline interesting. He should have limited Phil's input to phone calls between him and Susan, with perhaps the occasional implication that he might have been up to something with other people in Alaska.