I take an abbreviated version of that trip-Richmond to New York, on a regular basis. I've looked at going all the way to Boston, but the amount of time it takes is too much more than a flight takes, so I fly to Boston.
My advice to you is: bring your own food (drinks are OK on the train, but the food is inedible), and sit toward the opposite end of the car from the bathrooms, which are pretty rank by the end of the trip. Personally, the overnight trip would be awful, but I guess enough people can stand it that they do those runs.
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