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ND,SD& NE by train & bus ???

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Next May we hope to travel from Chicago by train (Empire Builder) to North Dakota, then to SD and NE by bus? We have been told that this is probably not practical so may have to hire a car.
Questions-
1.Where in ND would be the best place to get off the train to pick up a bus?
2.Where would be the best city to hire a car
3.We would want to hand the car in when we reach SW NE (Crete)Would this be much more expensive?
4.Which places are a must for our itinerary?I have read quite a few replies on the forum already and most of the interesting places seem to be in the west of the states.
We are interested in history, like scenery and the countryside but can't walk as far as we used to!
5.Driving in the wrong side of the car on the wrong side of the road creates arguments !!We have driven in New England (a nightmare!) before and NE (fine!) but would prefer not too much big city driving.
6.Would we have to book B&Bs or hotels in advance or would it be easy to find accommodation in May?
8.Importantly-what should the weather be like there in May? Warmer than Scotland?

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