three issues Ive encountered, all of which actually spin off the first
#1) Amy vs Dealer, the hint isn't very clear you require one of Serena's magic cubes that are described as a booster for telepathy rather than a generic magic booster for the player.
#2) I had $60 for 6+ weeks, then all the plots started requiring money at one time, and Serena doesn't reimburse the player when she says she will. So I had to pay the $10 for the date with Claire, $20 to buy the topaz for Serena, and had to come up with $50 (while having only $30 left of the original $60) to try to buy a half-off magic cube from Serena for the dealer fight.
#3) How to get the job should be a hint though to help avoid the "I have no money, Serena didn't pay me back when she said, and I can't advance ANY plots without the cash" issue. You start the game on day 1 with $60 and after 6+ weeks it wasn't obvious at all what I needed to do to "get a job" with the not a gift camera you get from Katie in the first couple days.
Amy vs Dealer (round 2) required you buy a $50 magic cube from Serena
Claire got her boss blackmail, and you have to take her out on a date (-$10) to move that plot ($60 total so far, with no income)
Kate is seemingly hard-locked with 4 consecutive Saturday afternoons at the pool, putting sunscreen on her back
Serena charged me for the topaz and doesn't reimburse (-$20, still no income)
Aside from the above, the models are nice, and while I'd prefer the option to help Amy magically lose the dick since she seems unhappy with it having been magically done there's plenty of other girls (Claire, Serena and Missy yum) to keep me happy and interested.
I got around the no job thing through a saveedit, and am now exploring as to how/what triggers getting that job so I won't have to cheat, or keep this thread open to search it anytime something comes up that isn't pretty obvious.