I played through the game twice, based on the girls reaction each time I think the 3 item rule is intended, you're supposed to give her the items you think would be the most meaningful.
The first time I gave her the shoes, the clothes, and the PlayStation. The second time I gave her the award, the picture with his dad, and the diary. She had a different reaction, there was more expansion in the story when you give her more meaningful items. I'm gonna play again so I can see the reactions to other items.