DEAN: So you’ll come home, do homework all weekend, then leave.
RORY: No, I can do my homework during the week or on the train coming home to see you, who I will spend my weekends with not doing homework. Plus, we can talk during the week on the phone constantly. Trust me, it’ll feel like I never left.
In real life, it’s a three and a half hour train trip from Boston to Hartford, requiring a change at New Haven. Then Rory would need someone (Dean?) to pick her up from the Hartford station for a thirty minute drive home to Stars Hollow. It sounds very tedious to do regularly – of course, she has to go back again every Sunday, so that’s eight hours of travel every weekend! That does give her free time to study though, I guess.
As it happens, Rory doesn’t go to Harvard in the end, and she has a car by then anyway, so this impractical plan never gets put into operation. It does sound as if she hasn’t thought about it very hard though.
[Picture shows South Station in Boston, from where Rory would need to catch a train. It’s a 15 minute bus ride from Harvard, so add a bit more time on for that].