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I've done many of the routes you could consider, including US 20 through Nebraska. We love the back roads and small times when we have time to wander, but I would still recommend staying on the interstates. Simply put there is a whole lot of not much to see across Nebraska and South Dakota. We have done most of the alternative routes, Missouri and Iowa's back roads will give you hills. Not mountains, just big hills.
The truck routes are great when you have the time to stop and explore. Late August is a great time to visit any popular tourist area like Mt Rushmore. The crowds are much less, with kids heading back to school, and the Sturgis bikers are mostly cleared out from the rally. Everybody should have that Rapid City area on their bucket list.
When time allows we like to stop in the welcome centers entering a state we will be spending some time in, or might on a future trip. We pick up some knowledge, and some brochures for things we might try to see.
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