[I've made your PDF clickable with the link below.]

Pretty good presentation. It's obvious you've put in lots of time. My comments are not comprehensive, but just general observations at this point. I have to ask, in regard to your not wanting "cookie cutter" landscaping, unless that term is somewhat better defined, it's open to misinterpretation. What does "cookie cutter" look like to you? Since it's the rule, not the exception that standard subdivision landscaping almost always includes common mistakes (creating barriers where there should be none; obscuring positive architectural features with vegetation... and the converse: not addressing lack of architectural detail; creating a hectic, unrefined appearance by incorporating an excessive number of plant varieties... or using such little variation that the landscape seems dull; failing to work out a pleasing, cohesive geometry to the planting arrangement and beds; building high maintenance into the scheme; forgetting to incorporate 3-dimensionality--vertically and horizontally--into the scheme; ignoring scale,) a yard full of these mistakes is what the term "cookie cutter" means to me. (I'm sure there are more common errors but those are what come readily to mind.) If you avoided creating all these conditions, I don't think you would have "cookie cutter" landscaping. Obviously, there's still lot of room for creating personality in a yard.

Is the fence opening at the back yard, right, a gateway, or just a temporarily missing fence section?

Is there an expected use of the back and side yard lawn areas? Or are they just for visual display? Is there a need for privacy other than what the fence or screening by tree canopy provides?

An excessive amount of featureless roof shows at the south side of the house and there doesn't seem to be an attempt to obscure any of it with tree canopy (large or small.) Is this intentional?

Here is a link that might be useful: Clickable Master Plan

Your description is exactly what I meant by cookie cutter - from an architectural standpoint our neighborhood has about 8 different floor plans so many of the homes look similar. From a landscaping, plant standpoint everyone gets the standard Silver Maple dead center of the front yard, and miscellaneous "pointy, prickly leafed" Holly near the porch and on either side of the driveway.

And that's okay because we knew what we were getting into. I just now desire to:

1. Personalize our landscape to fit our needs
2. Create more utility in different areas of our yard
3. Begin blocking some unsightly views
4. Provide a little more privacy from neighbors
4. Meld our home in its environment to make it seem like it fits and isn't just randomly placed their

The pictures are little misleading in that I currently do not have a fence in our yard. We will be getting one in a few months. The drawings I did show the outline as the fence itself.

The expected use of the back and side yard would be a play area for my son. Just a good place for us to play catch that's why I attempted to put the landscaping around the border and leave the middle open.

I don't think I would need any more privacy than what the fence and tree canopy would provide.

Regarding the featureless, south side roof, this was unintentional. I have a sewer line that runs down the middle of that side yard so I always get nervous when thinking of planting trees in that area. Maybe there's a good tree or landscaping that will get 25ft high or could at least obscure this some? I have two cherry trees not really featured in this layout (they're the left out trees beside crepe myrtles) maybe I could use there.

Thanks for the help

"2. Create more utility in different areas of our yard " "Playing catch" is the only need for utility you've identified so far. What else?

If the fence in photos is not yours, are you going to install your own fence that runs parallel and in close proximity to the neighbor's fences... like they are back-to-back?

"Meld our home in its environment to make it seem like it fits and isn't just randomly placed... " In general, trees will be significant in helping you accomplish this goal. You have some trees and are proposing more. The large, unbroken expanse of roof on the south side should be one of the places that trees address. I really can't see that two rose of sharon--being relatively small--would be capable of doing the job. Cherry trees might do fine. What kind of cherries?

Other than the photo of the house front, the others seem to be photos taken at oblique angles. They're fine as supplements, but they tend to markedly distort the appearance of structures. For helping us to grasp basic understanding of the space and structures, it would be good if you had square-on shots of the building faces, similar to the photo of the front. It would be helpful if they were regular size, too, as the ones on your project page are rather small. If they were posted directly into this thread it would be more convenient.
Not saying that you have to add these; just that they would be helpful for understanding your space, so therefore, welcome.

Will be out for the rest of the day; I'm sure others will chime in on your project.

I don't have any specific recommendations for you but I do want to recognize your well-considered plans :)

South side

East side (front)

Front yard looking out

South side view of backyard (notice sloped backyard)

[Copying master plan link again for convenience]

"2. Create more utility in different areas of our yard " "Playing catch" is the only need for utility you've identified so far. What else?
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Things like actually being able to live and play in the yard - play catch, sit under a tree and enjoy a drink, attach a birdhouse, maybe a tire swing, eventually when the tree gets big enough a tree house, perhaps a tree for my son to climb, etc. Those are the types of activities I could see us using our yard for. Currently I use it to kill ant hills and mow. Not fun activities :)
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If the fence in photos is not yours, are you going to install your own fence that runs parallel and in close proximity to the neighbor's fences... like they are back-to-back?
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Yes we will be putting a fence up. Along the back we will have to leave a ~5 ft gap and we can directly attach to our neighbors along the north side of our property.
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"Meld our home in its environment to make it seem like it fits and isn't just randomly placed... " In general, trees will be significant in helping you accomplish this goal. You have some trees and are proposing more. The large, unbroken expanse of roof on the south side should be one of the places that trees address. I really can't see that two rose of sharon--being relatively small--would be capable of doing the job. Cherry trees might do fine. What kind of cherries?
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That's something I had not considered. I currently have a Yoshino and Kwanzan Cherry tree at my disposal in my yard to be moved. Maybe these could go on the south side of the property to provide some coverage?
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Other than the photo of the house front, the others seem to be photos taken at oblique angles. They're fine as supplements, but they tend to markedly distort the appearance of structures. For helping us to grasp basic understanding of the space and structures, it would be good if you had square-on shots of the building faces, similar to the photo of the front. It would be helpful if they were regular size, too, as the ones on your project page are rather small. If they were posted directly into this thread it would be more convenient.
Not saying that you have to add these; just that they would be helpful for understanding your space, so therefore, welcome.

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I uploaded several here and hope that helps some. I am afraid my initial post was a bit overwhelming? Should I perhaps have broken my "regions" into individual, more specific posts?

Here is a link that might be useful: Landscape

Looking west from driveway to backyard

The new pictures help. Looking at a whole yard takes more time than looking at part of a yard. Placing all of it in one thread requires more time so be prepared to wait longer for responses.

You mention mowing as being not that pleasant. An alternative is to place some of the now lawn into groundcover. It requires being rigorous about not allowing weeds in the beds. While the groundcover is establishing it takes regular patrol, but once it's established, weeds are much less likely to invade so maintenance becomes less than mowing (as long as weeds have been kept out during the establishment phase.) Groundcover beds make sense below groups of trees and around shrubs or wherever you don't want to mow, such as hills or rough terrain.

The following notes apply to places I've marked on your plan per photo below...

A) River birch being grown a great deal for what shaggy bark offers, is better with more of it. I think a grouping of 3 trees--multiple trunk-- would make a better statement for the corner. Terminate the beds into the fence at 90*. While your curve keeps the curved theme going, it does not work out to have grass occurring behind the beds. It's impractical and won't look good like you might imagine.

B) There is such a radical difference between leyland and maple that your thought process (those being alternatives for each other) cannot be second-guessed. One can presume you're trying to screen neighboring property, though. I think here's where I'd opt to put the row of crape myrtles... at about every 10-12' on center, matching. I prefer them pollarded (as your photo of the pink one is.) I prefer a wider trunk system (as your photo of the lavender one is.) The dashed red line... there could be a groundcover bed below all trees, simplifying and reducing mowing.

C) Here you have an existing tree (we don't know what kind yet) that I'm indicating with darker green color (closest to letter "C".) Depending on what the existing tree is, I'd either get two more and create a threesome group of same (which might require relocating the tree) or...

D) I'd get 3 altogether new trees and create the group shown by the lighter green symbols. Shade trees or sizable flowering trees would work. Groundcover below would be nice. Regarding the crapes you are proposing here, I think they will be weaker looking than shade trees or larger flowering trees. At any rate, I dislike very much the idea of intermixing colors as you show. This will read as a little too cute and too 'country.' Instead, think of the whole group as a single item. You're just making it of parts. You wouldn't want a car with varying colors of fender, hood and trunk deck.

E) It seems to me like a missed opportunity not to display two small flowering trees in front of those blank wall spaces at the corner of the house. No one would be surprised that I'd recommend multi-trunk trees--like giant flowering bouquets --for in front of a blank wall. More trunks = more art. (The single trunk --though good for when a window is in the distant background-- reads weaker against a blank wall.) Hedges of low woody shrubs or perennials could underscore windows at either side of trees. Groundcover below trees and in front of the one hedge if more GC is desired.

F) Another opportunity to display flowering trees in front of a blank wall and change it into something more interesting and adding 3-dimensionality so that all the foundation planting is not flat up against the house... and as with 'E', screen a portion of the giant, naked roof.

G) What is the distance from lamp post to nearest edge of sidewalk? The amoeba shape of the bed does not read as a positive landscape contribution to me.

H) I moved this tree (if that's what it is) to the right a little so it is away from the other group and falls between the groups of trees showing in it's background (as viewed from street.) Seems fine to have a separate tree here.

{{gwi:45715}}

Thank you so much for the help. I am going to spend some time and give this proper thought and redesign some things. I will post back here in the next day or so.

Here's a graphic representation of some of the suggestions. It's very general; there are plenty of places and ways to massage and tweak it, including adding more detail. Keep in mind that its personality would be highly dependent on what plants are actually selected and how they are maintained. Hope it will help you think about the landscape scheme.

{{gwi:45717}}

You have to eat right, what about incorporating some edibles in the yard, like a edible peach or pair to hide the 5 foot gap. I think you could do a perineal herb garden near the house easily. I would try to reduce the lawn like yardvark with the edges just know those trees are right up against the house. I think some dwarf hollies would work well with your home color.