I know you've probably figured this out by now or given up on the game, but if you Talk to the third Jackie, who is Jackie Woo, and he will say "I'm trying to find somewhere to rent a motorcycle," and offer a lift. He will ask you to drop him off at Downtown. Your agent will call you to tell you that you did something right because he just talked to Jackie's personal assistant and Jackie wants to meet!
I filmed "Time Alien" & "Oscar Mike", so I then got the goal "Movin' on Up". When I arrived at the Headley mansion, Charlene told me there was a new agent named Marica Shaw that I should talk to. I saw Max Bling and others at the mansion, and I could talk to anyone but Max Bling (I didn't talk to them). After talking to Marica Shaw, I agreed to later meet her at her new office for a meeting. I then left to do Flower's Vauge photoshoot. After doing the photo shoot, I went back to the party, and, again, had the option to talk to everyone but Max Bling (but, again, I didn't talk to them). I then got a call from Charlene telling me to come to her office. I left the party, went and talked to her, then returned to the party. It was the same thing. I closed the game because I had no energy. When I opened the game later, everyone had left, just the real estate agent was there telling me the mansion was for sale.. Why could I never talk to Max Bling and get him as my agent????!!
You can have Max Bling as agent when getting the goal Movin' on Up :)
as for the STAR Awards you have to do the Wooden Cuckoo in order to unlock the feature. Once you have done that you must get 4-5 star ratings on projects 8 hour or more in order to stand a chance in getting nominated for an award ^_^