If you're south of highway 10, I'd be worried about invasives when opening up a section of woods. Buckthorn, honeysuckle, and boxelder are real problems. If it's maples you're cutting, the regrowth should be really attractive to deer.

On your 2 year old cut with the knee high grass, I would bet that you're not looking closely enough. If that was woods, there should be woody growth coming back. If there's no woody regrowth present, It's possible that the deer are eating it down before it gets a chance.

The key to managing openings like this is knowing what to look for, how to identify plants. You can make a big difference just cutting by hand in the opening, selecting for the preferred plants.