I'm in SE WI...not quite as flat as you, but I'd still claim "flat, flat, flat, bump, flat, flat". That said, I've successfully climbed mountains in Mallorca and roads with really big, long bumps in Italy. I tend to believe that if your riding style supports long stretches of continuous spinning, given the right gears, you'll get up that hill.
For our first trip with hills, Mallorca, in retrospect, our best substitute training was riding our gravel, old railbed bike trail. In one direction it has a slight grade and you have to pedal against a resistance to keep moving. On that trip we managed two mountain passes--on hybrids.
For the Italy trip, we did the Spinervals thing this winter. The "hills" in Italy were worse than the "mountains" in Mallorca--much steeper and just as long and tall. Except for DH getting sick, the hills were accessible to us flatlanders. When we hit the roads, we travelled over to SW WI (between Bluemound and Dodgeville) and road the hills there (real hills not mountains calling themselves hills). Even though we do that only once or twice before a trip, I believe it pays off. I'd vote for doing the Indiana ride.
Elsewhere on these boards, some of the women have mentioned that after a point, doing distance is more mental than physical. For flatlanders, I think hills are, too. If you see them and panic, you're toast; if you see them, and shout, "Oh, cool! The road goes up so I get to go slower and be on my bike longer!" then you'll do fine.
The best part of hills for me now is the changing perception. Even on a single 100K hilly ride, my definition of steep decreases and my confidence increases as I ride. Perhaps, you'll see the same?
Go for it! You might just surprise yourself. In the meantime, keep riding and slowly build up the distance.



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