I got the train once to Preh which I believe is a little further than Pitsanulok (My geography is terrible.) I would not get it again, as it is dated and uncomfortable and shakes a bit too much to get any sleep. The private bus companies (not the tourist companies) are by far better. If money is not too much of an issue, I would get the plane every time, I reckon there's more to see and do in Sukkhothai than there is on the train, and if you get the overnight one you won't sleep and will be too tired to enjoy it when you get there.
I don't know if there is a sleeper car on the train. If there is it might be worth considering, but I'd still go with the plane.
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