I think you’re missing the point.
Bowdoin, like Brown, is unlikely. While I love your profile and suspect you’ll get into a fine school, there are no assurances.
You’ve been given lists of scholarships but told to be careful. It’s a time suck, odds of winning are low and amounts are low.
Moneys come from colleges.
You are not chasing prestige yet every college you list is prestigious and doesn’t offer merit aid.
I hope the NPCs are right but often people fill them in incompletely.
You say you are upper middle class and that means different things to different people but upper middle class is not getting Brown at $32k.
You are potentially the student who comes back in 8 months and says I got into college but cannot afford to go.
Find schools to supplement your list. Whether it’s an Arizona or U Maine or SUNY New Paltz that might match Rutgers. A Hendrick that might match Rutgers tuition through its Flagship. Sewanee - one of the top literature LACs that’s aggressive aid wise or Furman may not hit your # but are aggressive.
I hope your plan works out. But you are overreaching, potentially financially and if you are, while part time and summer jobs are nice, they don’t fix that delta.
Perhaps you are not upper middle class - by your definition yes but not by most.
I’m saying - please protect yourself and add a few schools - like a Maine, Alabama, Arizona, Ole Miss (fine English) that will 100% be budget compliant. Also Kalamazoo is a fine LAC and is aggressive as is Depauw but not assured like the publics mentioned to hit cost but likely close.
You need insurance - admission but most especially financial.
I hope it works out as you think but you are missing some key components that need to be planned for.
You don’t need more scholarship ideas. You need a contingency plan unless mom/dad can pay more.