I'm one of those people who doesn't like to drive. 2-3 hours is probably my upper limit mentally. I tend to take breaks every hour-ish so a 3 hour drive can easily stretch into 4-4.5h with those included.
My usual would you drive vs would you fly route would have been Boston-Manhattan I took every few months.
It would be around 5 hours to drive vs drive 10min to regional rail station, park for a day, train 40min to downtown Boston, subway to Airport, fly 1hr to JFK, 40min for Airtrain + LIRR to Manhattan. Flying takes just as much time but I'm driving myself for a fraction of it.
I usually got basic econ RT tickets on Jetblue for under $100 and it was probably even cheaper if I could fly out of Worcester regional when they had those flights to JFK.