Should I push for an Ivy League School? If so, which ones?

You should try to visit Philly if you can. You can tour campus and have lunch with a current student to get a better feel for whether Penn is somewhere you can thrive. Penn is wonderfully compact but it is an urban campus. There are major intersections, noise, and homeless people. We enjoy the vibrancy of West Philadelphia but you may not. Figuring out whether you like the urban environment or prefer a quieter campus is helpful to know before you apply especially if you’re thinking of doing ED. Best of luck to you.