I worked on getting Max and Anne's spring break event for several hours, and what finally worked for me was skipping every event except those that built Max's relationship with Anne and the battle of the bands, and making sure that the Halloween event had Anne as the murderer (what you find in the victim's pockets determines that; for Anne, you need to find a mini recorder). Also, I focused exclusively on rest, Rational, Organized, and studying (I slept in on weekends, napped once during the week, and split the week between working at the bookstore/library and the data collection/Physics class jobs, the chess and tabletop RPG games, and studying on the days that don't let you build those skills). At week 15 my grades were over 600, and Organized and Rational were over 200, and my relationship with Anne was at 95. During this week, a new scene featuring Anne and Max in the bookstore/library (one I didn't see mentioned in the help guide on page 1) played and I got up to 100 relationship. The spring break scene then triggered. On other playthroughs, I had 90 or 95 points, and well over all the other requirements, but until I got the bookstore scene and got up to 100 I never got Anne's spring break gallery achievement.
I don't know that you HAVE to skip the other events, because I'm not sure what finally triggered the bookstore scene, but I did just because I wanted to finally get the achievement. Likewise, you may not have to get to 100, you may just have to pass this scene, so Halloween might not matter. At any rate, this worked for me, so hopefully it will help someone else!