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.

Wow thank you everyone and definitely keep them coming! Some great ideas it really gave me a visual of what it can actually look like. Here is another photo. Yardvaark if you can suggest where you would plant the trees. Vstavay wow I would never even think of doing anything to the area along the lampost - awesome! I also love the arborvitaes along the side. NHBabs great helpful tips! Especially about planting evergreens. That's what I'm afraid of is that in the winter it can easily go back to looking dreadful.

Great advice offered but IMHO rather than the Victorian looking door I would get a full view storm door & a simple modern style exterior door & paint it a nice color...as NHBabs was saying about planting away from the house - I took out old shrubs that were right next to the house & planted prettier ones about 3-4 ft out & I love it...can get to the windows, my hose outlet, & maintain both sides of the shrubs...

Since your large tree is near the street, I think you could place a small tree off the left corner, in a groundcover island bed, at the outside of walk. Unfortunately, no room for tree at right side because of drive. Drawing through your existing tree (for my ease) is not a suggestion that you get rid of it.

I like the idea of full view storm door. (I don't think Victorian look fits.) Also concur with placing plants somewhat away from wall. 3' to 4' works well for most low/medium foundation shrubs ... depending on the total front-to-back depth of bed (which should be in the 6' to 8', or larger, range.)

I wonder if a coordinated color, different from the trim color, would look better for the garage door.

Again, very helpful. Yea we will be replacing the front and garage door so any more suggestions about that are appreciated. What do you guys think as far as colors for flowering plants that will match my brick? Red family, pink , apricot?

Personally, I wouldn't worry about flower colors matching, coordinating, etc. If we're speaking about annuals, there are a couple of change-outs in a year's time. It would be rare that flowers actually look BAD. Gravitate toward repeating/refining the successes and it will be fine. The only way to make it look less good is to mix a bunch of different flower types and colors together into a busy mess. It will be a clearer, stronger statement if you use one kind/color of annual at a time. Insofar as perennials are concerned, pick a single type for a single purpose. If it turns out that you're not happy with them, change them all to another type. Use the back yard to stockpile a couple different types. Most can be easily and rapidly propagated using simple methods, so you only need to buy a few samples to turn them into large amounts.

Yardvaark, that's brill! Thanks so much!

As far as colors of flowers, I wouldn't try to match the color of your brick. I'd do the exact opposite - contrasting colors to your brick. If you try to match, you might get something that's close, but not quite. And that would look worse.

I would definitely not do pink. How about a clear, strong yellow-gold, white, and blue or purple?