Here are some more pictures

It would help if you'd create some uniformity in the bed line of the wooded area. The groundcover that's in it is a nice lead-in into the woods. But it seems strange that all the trees are not in the bed. Instead grass dips in to the sides/behind of some of the foreground trees.

Rather than placing any screening fore of the wooded area, it seems better to me if you place it at the back side ... so you're not cutting off your own view into the woods. What tall, shade tolerant shrubs grow there and would tolerate being at the back edge of the wooded area? Yew maybe for one. Is there a tall buckthorn that is not invasive? (I don't know as there are many buckthorns and some of them are.)

If I lived there I would have to have some screening from the neighboring properties.

The picture of the back of the house is too small to be useful. But it doesn't look like any of the plants there make sense ... either their placement or type.

Thank you yardvaark, this is very helpful. I like the idea of placing some shade tolerant shrubs in the backside. There is a creek in there as well. But with the right type and placement, that may do the trick. Also I am glad you like the ground covering. In front of the ground covering, that is a garden bed that usually gets flooded for 1-2 days when it storms. Do you think I should try to get rid of that bed and replace with grass? Also what type of screening would you suggest between the neighboring properties?

I think you should remove any frontal beds (save an isolated shrub or such) and let the groundcover come forward such that it could encapsulate the trunks of all front trees. This would entail the creation of a new bed line, killing a strip of grass at the front of the bed, mulching it, and allowing the groundcover to move/spread forward.

There are probably many tall shrubs which you could use to create a screen between yours and the neighboring yards. Look around where you live and see what looks good to you. Then, get it identified. (There is a forum for plant ID. You'd need clear pictures from varying distances, including close up.) If you're interested in hedges that bloom over a long period of summer, look into panicle hydrangeas. There are many that work for hedges.

Thank you so much! This helps a lot. Here is another picture of the bed I was talking about when it gets really rainy. So you think I should completely get rid of that?

Drainage is a separate issue. You can fix by filling low spots and making sure no high spots damn water from leaving via its natural path. But yes, I think you should get rid of the tall things that block view into the groundcover and woods. Clean up the trees within the first 20', or so, of the wooded area for a cleaner look... meaning remove low hanging limbs. But leave them alone at the back portion of the island as they contribute to the screen, which you'll beef up with tall shrubs.

Thank you so much for your help! I think this these are all awesome ideas. I will definitely take this advice!

One more question, by adding shrubs do you mean shrubs like limelight hydrangea (which I love) and will lose their leaves in the winter. Or shrubs that will stay green all year long? Also, should I replace the pines behind the swing set with spruce trees that are a fuller?

Saw an article re Michigan wooded area and though I’d pass it on

Spring Blooms, Pink And Yellow Flowers
"Dream Team's" Portland Garden
Hugh Stephens
,
The garden is particularly glorious in early spring, when daffodils and spring ephemerals begin blooming before the trees leaf out. Bloodroot, trillium, Dutchman’s Breeches, wild ginger, azaleas, Solomon’s Seal, and twinleaf abound. The soil is perfect for rhododendrons, and many grow as tall as 20 feet high. (Photo by: Hugh Stephens)

Trying to post pic not letting me, probably come up with 10 pics of the same, here we go

Thank you, that is really pretty!!

Whether shrubs are evergreen or deciduous would be up to your personal preference. Most people are not using their back yards much when it's cold and leaves are off of the shrubs.