Sounds like a workout, but also a good day's work. Fortunately, I have several choices as to loops on local roads. One is mostly flat, but the others are rolling hills with a few flat stretches. I ride compact double chainrings on all my bikes, but I usually don't have to drop to the small ring except on the steepest hills, but those hills do bottom me out.

Iowa is a lovely state with nice folks. The northeast is actually quite hilly as is the country adjacent to some of he rivers. Having lived in neighboring Nebraska much of my life, oh yeah, wind is a big factor. I'm sure you'll love it, though.