Notice that both designers removed the shrubs and grass and filled the entire bed with ornamental plants. Good choice. Regardless of what you plant, start the planting outside of the rainshadow caused by the roof overhang. That will be better for the plants and give you space to do maintenance such as washing windows. If you stand across the street opposite the front door and take a photo of the whole yard side to side, you may get good suggestions for tree placement. (If it's too wide stand in the same spot but take three photos: 1 straight on, one pivoting right and one pivoting left) I usually prefer trees not in line with the front door since as one grows it may make the entrance more difficult to see. I also discourage the use of rock mulch in areas like Chicago that have to deal with heavy rain and snow removal since they will get moved around and will need to be moved off the drive and walk and out of the grass. Your lawnmower can fling stone hard enough to do damage. For the downspout, if you want to plant a climbing rose, add a hard prune clematis with it to best hide/distract from it; many roses have rather sparse foliage. Provide an ornamental trellis and clip the rose to it so the rose doesn't grow around the downspout. (One of my more vigorous climbing roses sent canes between the downspout and the house which needed to be cut out.) You could also do the same between the windows and at the far end. Think about having something that won't be just bare in the winter, whether it is evergreens, shrubs with colored bark, a tree with a great winter silhouette out in the yard, or ornamental trellis that will look nice in winter once the clematis is cut off it. Winter can be long in zone 5! Whatever plants you decide to put in, research their size potential on reputable sites such as the Missouri Botanical Garden's plant finder. Nursery tags tend to give size at 5 years, but many can get quite a bit larger.

I also vote no shutters. Please don‘t take what I’m about to say the wrong way : ) ... Yes your home is old, and all the other homes in your area may have shutters....however your home was never designed to have shutters. You can tell by the placement and design of the windows. While shutters can act as eyebrows for your windows, the original purpose was to “shutt”. If visually you can’t shut and open the shutters it will look off, and therefore, wrong. Bellow I illustrated what your shutters would need to look like if they propperly fit your windows: See what I mean. Every shutter needs a window, but not every window needs a shutter. Your home won’t look “off” without them, they will look right. Your windows on your first level are wood, leaded, and original- let those shine! Now, as far as trim and door color...I’m pegging you home between 1910-1920....possibly early 1930?? When choosing trim and door color, go historic. I went and did some quick research for you on archive.org. You can also find historic colors at any local paint store. If you design your homes exterior in the era it was intended, it will never look dated. Yes, many of these colors seem bright (not everything was pastel back then as we usually think...) Also remember that your colors will be outside, bleached from the sun. Always go darker and more colorful than you think. Choosing your color outside will help :) 1920 https://archive.org/details/TheMuraloCompanyInc.C1920 1910 https://archive.org/details/RuekelBestQualityMixedPaint 1930 This one is for galvanized iron, but it could still easily be applied to your door and trim. https://archive.org/details/GalvanumForGalvanizedIronTheOneOutstandingPaintNotedForItsAbility Here are two examples of historic homes with proper color pallets, see how they come to life! Notice while this home from 1929 has shutters, visually they can all close. Hope that helps, and good luck!

Here's a few additional pics of the space to give you a better feel for it as a whole!

I want to paint the siding and shutters. And I’ll post a picture of the brick. The second photo is the back of the house. The brick in the front is faded due to years of neglect from previous owners and weather.(Our house faces east). In South Texas the summer sun is extremely hot (110 degrees temp.) so the back of the house is not as faded as the front. My husband wanted to paint all the brick but I don’t want to.