Congrats on the new home! It is definitely looking better with your current work. Here are some random thoughts that occurred to me while looking at your various photos. I'm interested in seeing the photos Yardvaark requested, and also one that clearly shows the entrance from the sidewalk, when standing directly out from the door. I am another who wouldn't paint the brick since it involves increased maintenance, especially since you have chosen low-maintenance hardie board siding, but you are the one who will have to deal with it. However, I would wait to do this until you have worked out a planting scheme since it may turn out that the current brick color makes a better backdrop for the plants than the light color. Once you have a plan, then if you still feel it will look best, you can do the whitewash before actually doing the plantings. As others have said, I think one of your biggest challenges will be to find a way to make your almost hidden entrance easily seen by visitors. So you will need to keep that in mind with whatever you decide to do with landscaping. For instance, planting an evergreen at the left house corner may hinder the visibility of the entrance from some angles. IME, planting along the driveway edge won't prevent folks from driving off the edge, it will just mean that your plants get driven on. It also presents an issue with where folks walk when they get out of the car; if you have plantings lining the drive, and the cars fill the drive, there isn't anywhere to walk, so grass or a walkway from the street to the door might be your best choice for the driveway edge. Soaker hoses on a timer or with you turning them on as needed will help with keeping things watered. Since they go under the mulch, they won't be visible. Getting the timing right will need to be worked out based on what you plant and your soil, but here (with similar rainfall) I usually don't need to do much if any watering on established, mulched gardens. Rather than just getting plant ideas on line, go to the Chicago Botanic Garden, which is world class and grows research plots specifically to figure out what plants grow well and look good (disease free, etc.) in your area. Go often, like every 2 weeks so you can see what looks good at different times of year. Take photos of plants and their labels so you know what to look for when you have a plan. As for the mulch and paver edging dilemma, I might just add a light layer of a mulch color you like for now, with perhaps some annuals for color, either in the ground or in large pots. Your ultimate plan may have a bed that looks quite different, and once you have a plan of what the planting area will look like and what types of planting and hardscape changes you will plan to make, then you can remove mulch and edging. It just seems a bit of a waste of your time and energy to do much with this area for now. Early fall is a great time to plant, so if you don't get things planned and planted this spring, you can do prep this summer once the plan is in place and plant in September. The annuals will add interest for the summer so it doesn't look so stark.

I see no advantage to any of the raised bed that's been added... but only negatives. It would make anything that you plant too tall for the stoop and start hemming it in. Instead, you could plant something low and cover the edge of the stoop with a groundcover instead of the block "curb". I would basically be shooting for a non-smothering look. It would be helpful to make the grade in front of the stoop level, across its front. I would remove the brick at the sides of the step. They are fake cheekwalls and not needed.

Some of my inspirations!

As I mentioned before my property was damaged in a fire and while I was fixing the place I wanted to somehow update the curb appeal. Many of you said the exterior wasn't a pressing issue. I've kinda cooled on the concept of a ventilation curtain cladding but still want some improvements to the front rooftop deck to make it more usable in the hot summer months and to provide some protection from the rain and wind. Do you think a shade structure up there will enhance or detract from the look of the place? I did my best to photoshop it into place. I'd use curtains to soften it and to make it more cabana-like. It is a louvered roof that opens to for more of a slatted trellis. I also need to raise the handrails about 8 inches to make it safe up there so maybe I'd add 1-foot tall ombre sand-blasted panels of glass that gives the effect of white smoke rising around the rails. BTW... I can make that shade structure up there ANY color I want. The frame can be one color and the interior roof with the paddles closed can be another. If I do it I would match the frame to the existing galvanized metal and make the ceiling white. Any input would be appreciated!