I drive ~4 hours to EWR. I hate it. Somewhere around the 2-2:30 mark is where I start to lose my mind. I could probably do it for the rest of my career. Even with 0500 shows and 2345 releases effectively being red eyes on either end of the trip. But it is miserable.
Still, its much easier than driving an hour to BOS and then worrying about getting on or not. Or getting back.