Ask this question on the New England forum also. Your part of MA has winter moths that can defoliate some kinds of trees more than others. There are a number of folks from zone 5 MA who visit the New England forum regularly and will chip in. I'd include a question about winter moth and other pest susceptibility in your post. There aren't winter moths in my area so I can't help with them, but I know that cherry trees around here are susceptible to a wide variety of pests and tend to be short-lived. There was a similar question there recently that might give you some ideas even though her size range started smaller than yours. You might want to consider whether you will want a mix of trees which will give you a longer period of interest and some protection from losing your entire shelter belt if there are disease or insect issues vs. having a more uniform look to your row of trees. You are making a good choice not to look at callery pears. They don't do well with the wet snows that often happen in New England. This is from last fall's Thanksgiving storm and the homeowner had to remove about half of 6 trees.

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.

Like Yardvaark, I would widen the walk to 4-5’ wide and use the rock mulch or pavers in the area to the right of the walk with pots of shade tolerant plants for color, though you will need to water the pots. The overhang will make this dry enough that weeds in the rock shouldn’t be much of an issue. The foot isn’t wide enough for in ground plants, especially under the roof overhang. Widening the walk will keep the pots from making the space feel crowded. In planted beds I would use shredded bark mulch instead of rock. Bark mulch is better for the plants, and rock mulch will eventually get weeds from seeds that blow in, and it is far more difficult to remove weeds from rock mulch, especially if there is weed fabric which is also hard on the plants. I think the narrow holly emphasizes the narrowness of the spots to either side of the garage, and would choose a more rounded form that stays shorter than about 3’ so that it isn’t interfering with the light. You are correct that the Japanese maple isn’t well placed. I like Yardvaark‘s sketch with trees off both front corners to frame the house, and I think the maple is too small for that spot and would choose ornamental trees or tree form shrubs that are larger than the maple. What is currently at the left corner appear to either be too small or too close to the house to allow room for growth. Is there a back yard spot where you would have a good view of the maple? I would make the front bed deep enough for more than a single row of plants, such as some naturally low shrubs in back that won’t impinge on the windows and an evergreen groundcover with spring bulbs and perhaps one kind of perennial in a clump toward the walkway. At least something at the front of the house besides the groundcover should be evergreen.

I have a mixed shrub bed that is probably 15’ x 60’ and am in a similar zone. If you want arborvitae or Rhodies, just plan to spray with a deer repellent. Some are oil based and some can be mixed with a substance like Wiltpruf to prevent it washing off so that it only has to be renewed every few months unless there is new growth. I second the comment about blue spruce not being worth a long term planting in the humid east. Mine after 10 years are bare on the bottom and losing needles and shoots on the top, so I will take them out in the next few years. My preference is for having a rhythm of repeated characteristic plants down the length of the bed rather than clumps of one kind, and then I fill with variety. Here is a thread where about half way down I added a couple of posts with photos and an explanation of my plan and goals, so rather than rewriting the whole thing, I am sending you to the link. https://www.gardenweb.com/discussions/3113384/shrubs-for-privacy-along-a-fence#n=22 I have listed plants I used and even after 10 years I am generally pleased. Some plants have not done well (Pieris and Cornus are much beloved by the voles and don’t live long without roots) and as mentioned above, the blue spruce are disease prone. By now many of my groundcovers and perennials have been shaded out. Right now it needs editing, but I have spent the last year dealing with a terminally ill family member, and it has done surprisingly well with quite literally no maintenance. I will do some editing this fall when it is a bit cooler, and if you can find dwarf versions of other evergreens that are less popular with deer if you don’t want to spray, that would be good. My Norway spruce which isn’t in my shrub border, while lovely, at something like 25-30 years, it is huge, perhaps 25’-30’ wide and well over twice that tall. So if you want to use a spruce, look for ones that grow more slowly. For instance, there is a slow growing version of Serbian spruce/Picea omorika as well as one that looks bluish, so look for those. I went to all the nurseries in my rural area and chose from what was available that suited my needs since I wanted somewhat larger starting plants. One of the fastest growing plants I put in were panicled hydrangeas, and between their ability to gain size quickly, their need for little attention after the first year or two, and their months long bloom, I would use these again in any similar garden. I deliberately used more than one color and texture of evergreen for winter interest, particularly during the long fall and early spring when there isn’t snow. My cover photo shows a piece of it during this stage if you click on my name. If you have questions, feel free to ask.