Maryland - you should be in zone 7. I also like the brown; it's fitting for the style of house. As for landscaping, you can lighten up the heaviness of the old pines with the addition of a lacy dogwood or one of the many beautiful varieties of Japanese Maples out at the sunny edge of the stone retaining wall. The lamppost bed would look nice with something simple like Perovskia or Walker's Low Nepeta - both have silver grey foliage with lavender blue spikes of flowers. I'd resist the temptation to color up with the usual assortment of rhododendrons and azaleas - beautiful, but just everywhere in the Mid-Atlantic. Sometimes less is more.

Thank you very much for the constructive replies. @yardvaark @ninigret - brilliant on the parkway/boulevard strip. Your picture @yardvaark could not be more helpful. The trees flanking the boulevard strip are not properly sized for the entire neighborhood and it is a species that does not like the soil so roots are at the surface and choking out grass, not only on our property. Also, the height is almost maxxed so HOA cannot remove any more lower limbs. A problem for us as well sitting on the front porch. We are going to inquire with the HOA if we can plant a new species that will give more height and clearance to replace the two on property. I also received local opinion to replace choking lawn on that boulevard strip with myrtle (vinca) and tuck some flowering bulbs in for spring color and small white annuals could be tucked for summer color. The fence/gate is a beast to care for as it is all wood and many caulked joints that get hit by irrigation in warm months and piled with snow in cold months. I have a consult with with Walpole Woodworkers to see about an AZEK replacement fence and newels. We think it would be nice to replace fence with a true picket style to differentiate from porch railing. The 2 swinging gates are painted mahogany, one rotted out and fell off. It is a costly refurbishment, as $800 was already out in and not all rot remedied nor has it been repainted yet or routed for hinge. Even fully restored these gates come with a costly future maintenance schedule, as we don’t do any of this type of home maintenance ourselves. So we are thinking of removing the gates since they primarily stay tied open and do not seem to us to contribute much to the overall look & feel for their cost (but looking still on opinions of gate). The color you suggested @yardvaark cannot be placed to the front side of the fence as you sketched, because it is right at the sidewalk line. However, the backside of that fence is an 18”width of myrtle ground cover and thinking a long decorative, lightly elevated zinc planter box floating on the myrtle ground-cover, filled with seasonal annuals could bring the color we need and spill through the rails. Going to play with that. @houssaon definitely going to explore accenting the architectural elements you mentioned with our new siding/paint job. Also considering a metal roofing accent above front porch when we re-roof. Your picture is a great inspiration photo for me and I saved it to my file. Thank you again.

I also thought of incorporating a low planter behind the plants in the courtyard area (like the photoshop image) or even some potted plants among the in-ground plantings to play with the heights and give it more separation of space but still primarily living/green.

agree w/flo. you've got to do something w/the chain link fence. is it on your side? if not, maybe check w/the neighbor to see if you can attach something to it. if it's on your side, go for it. Before/AFter https://andthenwetried.com/2017/09/how-to-convert-a-chainlink-fence-to-a-wood-fence/ even adding the bamboo screening would make a diff. when you get that chain link cover, then you can bring in some potted plants: maybe a privacy screen? Wayfair has a bunch of ideas https://www.wayfair.com/Fence4ever--Metal-Privacy-Screen-F4E-L3361-K~CGDH1000.html then when you do that, maybe you can make up a lounge area. you have that area w/all that mulch. would be better if you removed it and put down some gravel, or DG or even large cement pavers . against the fence, do what flo showed you with large plant containers. you can't have a flower bed if it's concrete, here: so get the material to cover the fence, and bring in some colorful planers, tall plants and line them up. (try some bamboo plants or Arbor trees) Set these planters against the chainlink (which you will cover up w/something) and for that mulch pit, edge it out, remove the mulch and do something w/the center area like shown in the pics or, remove a lot of that mulch and do what they did here: