Don't know about Judy, but
No academic or sports scholarship money from Ivy League. You never knew how rich and privileged you are at around $150,000 / year / GROSS household until you get socked with paying $50,000 NET of $60,000 / year sticker-price tuition + R&B for 4 years. The whole US News and World Report highest ranked / highest tuition mania is on borrowed time. How much will it really worth to possibly impress some corporate HR gatekeeper stooge?
Idyllic Naperville isn't to be confused with Rahm's murderous Chicago, and perhaps Boston... Philly, NYC, Providence and New Haven, too.
The Ivy League has less cachet in the Midwest than you may think. Many of the top of the class types are elated to go to U of I or many of the other "flagship" colleges in the region, especially Ann Arbor and Madison. Just plain folks, without the pretentiousness. A lot less of the "cut-throatism" in academic endeavors, too. Ivy League for many top-of-class Irish Catholics in the area is spelled Notre Dame, where one of Judy's long-time high school running rivals is now on the roster.
Winters in the Northeast may be worse (colder, snowier, longer, more depressing) than the Midwest, and Oregon a big improvement as compared to either. Many area high school parents are waving the kids south or west to college, and will be joining them soon in that area as they move from the financially collapsing states.