You will develop a better feel for it with practice. While I know there are some elevation changes in the area where you ride, it's still relatively flat. Once you start doing some rides south of Indy, you'll get a lot more practice with it.

I'd also say that momentum only gets you so far in Indiana, as I wouldn't describe the terrain as rolling. Do the second day of the Horsey Hundred in Kentucky, and you'll understand the difference. Here, the hills aren't as constant and they can be abrupt and steep, so while you may have a bit of momentum going into the hill, it is unlikely to be enough to get to the top. In fact, it may barely get you up halfway. I actually tend to rely less on momentum with some of these steeper hills and more on choosing a gear at the outset that will allow me to set a sustainable pace up the hill. I do not keep the same cadence on those hills that I use on the flats. I would blow up if I tried to do that. Rather, I get in a relatively easy gear, take a deep breath and then just pace myself up, susatining a good balance between aerobic and power outputs.