“He did work for most of his junior year so that might help”
This does mean something. It’s not the something “plus” and would seem an affectation for a family that has sufficient income that working seems to be an arbitrary choice compared to other activities the child might be excelling in (say swimming to national level times). But, for another kind of family, in a less urban/competitive environment, working might show commitment to family, effort, and, depending on what he gets out of the work and what he contributes, leadership and learning.
As others say, superficial lists of lots of activities one does at even a high level for a school are not enough. Being highly capable, having accomplishments that show those capabilities, and being unique in the applicant pool. Uniqueness isn also not enough, because the school may not be looking for your brand of uniqueness (or they may have someone else who fits that category).
Also, I hate the advice not to try. It’s advice that strikes the less connected harder than it does everyone else. And those 60 schools that meet full need – they’re a real benefit for the families who qualify for need, if a child can get in to the school.
The key is to have a satisfactory backup plan, a certain one.