Are you planning to dig out enough grass to create your border planting? or were you hoping to push the woods even further back?
If the first.... we can probably help you... if you were hoping for something that would out compete the scrub growth in the trees... then... that would be a major undertaking.
I like the idea of planting some nice rhododendron...
And... take up additional grass in front of the shrub planting for a bulb bed...
Maybe a nice stand of blueberries as well?
And while we're discussing shade tolerant shrubs for indiana... I always did like the look of indian currant "buckbrush".
https://www.uaex.edu/yard-gard...