Harvard Tuition and Inflation
This movie came out 23 years ago. In the classic bar scene Will says to Clark: "In about 50 years you’re gonna start doin' some thinkin' on your own and you’re gonna come up with the fact that...you dropped a hundred and fifty grand on a fuckin’ education you coulda' got for a dollar fifty in late charges at the Public Library."
Currently, four years at Harvard (tuition, room, board, and fees) totals about $300K. So for the past 23 years tuition has gone up about 3% a year, so while it's still incredibly expensive it's only increased at the standard rate of inflation. Of course, as Will would probably point out $1.50 in late fees in 1997 equals about $3.00 in 2020...so he still got the better deal.
Food in Films: The fellas know that America (and Massachusetts especially) runs on Dunkin'. And I don't know what hamburger stand Will and Skylar were at, but those burgers looked freakin' fantastic.