The care package is a more elaborate version of what Luke brought Lorelai for the Bid-on-a-Basket Fundraiser when they ate a picnic in the gazebo, as if Jess is trying to give Rory even more. It might be another sign that he is paying too much for her or offering Rory too much. He’s all for the big gestures – similar to Dean and his gift of a car.
The food is brought in a box which once contained bleach. I’m not sure if there’s any significance to that, but it’s provocative (sperm is often said to smell of bleach, for example) and slightly off-putting.