"I wanted to create a "woodland" front yard but realized I have a large space to fill." Why would having a large space to fill prevent achieving your goal? You don't need to buy large plants in order for them to grow large.

It seems to work best if you have one thread per general area for which you're seeking help. Not sure how the driveway fits, but if it's a part of the front yard, it could be discussed in this thread.

In general, your photos are not good for conveying the details and overall layout of your property to those who have never seen it before. You should begin with a square-on photo taken from a central position, from far enough back that the whole front yard can be seen. While standing at the same position, pan the camera right or left if needed to capture those areas. Move closer and take additional photos to show what's in front of the house. All the photos should be in focus and well lit.

The issue you have with wire grass might be better explored on a weed or regional forum.

Don't plant tall trees under those wires. I know it seems obvious but many people make that mistake.