That's something I missed in the beginning, even before the last update. You need to talk to each worker in the office to collect the data, even the IT guy, who doesn't give you any data. The easiest way to see if you got all needed data to report to biff is that the game should advance automatically from day to evening after talking to all workers in the office. After that just head to the secretary and talk to her, after that go to Biff. You need to do this at least once a week, you can do it more often to progress faster from Biff level 2 to 3.[...]For reports, click on all the workers even the IT guy with your zip drive.
After reaching level 3 with Biff I got in the following week again the black swan photoshoot even though I already got 24/24 scenes. After doing that again the new content happend always after waiting one week ingame (did progress every monday in my playthrough: event -> new photoshoot 1st part -> new photoshoot 2nd part)