IMO, you must remove all of the existing shrubbery and replace it with things more promising. The existing shrubbery is wounded, downtrodden and has little chance of recovering. Plus, it was not chosen for low maintenance or excitement. Just start over. You stand a much better chance of making something good out of new plants ... planted a little farther from the wall so they have room to grow. A retaining wall is only necessary if you need to fix the grade for functional purposes, which doesn't seem to be the case. Instead, compensate for the falling grade by using a larger shrub at the low end and lesser height shrubs as the grade rises. In the area around the porch and farther left, you could get away with a single type of plant. (Any hedge that is part of a foundation planting should be trimmed level, not parallel to the grade ... so as to make the house appear stable.) Some color are around the entrance could help cheer up the overall scene. You really need to learn the proper way to trim shrubs as it will make an astounding difference. In order to keep the lower foliage, shrubs must be trimmed wider at the bottom then they are at the top. Of course, select varieties that can stand the existing light conditions as well.

I prob won't be much help because I hate your neighbors look. It's like a row of stuff that is currently small, but I can see are varieties that will become enormous (arborvitae, mugo pine, grasses) crammed inside another thin line created by the fake rock. Gack. Looks like gramma shopped at Home Depot. A couple of thoughts. First - I admire the fact that you already realize that your neighbor doesn't have the winter months working for her with her plant selections. Good for you - your instincts are correct. Darker colors make an item look smaller - they recede. Lighter colors make an item look larger. The lighter your house color, the larger it will look. It's hard to tell how far back your house sits from the road, so an opposing perspective might be that you could make your house look like its farther away by painting it a darker color. Remember the light grey roof - whatever color you decide to paint the house - the roof is part of the total look so you need to take it into account. Taking lots of pictures is a great way to see what you can't see by standing there in person. If you take digital photos, you can blow them up to 8 x 10 and print them in black and white off your computer and sketch the landscape right onto that. Don't cover up the windows and front door with improper selection of oversized shrubs and trees that won't fit the size of the house in 15 years. This is not inviting - make sure your front door can be seen. Make sure that shrubs are placed at least 3 feet from the house. This defies everything you've seen in new landscaping where small shrubs are planted 12 inches from the foundation but you will be glad in the long run that you can walk behind your shrub border to do plant maintenance,home maintenance, clean windows, make sure burglars don't have a hiding place. And the roots won't grow into the foundation causing you to have to re-waterproof your foundation in years to come. Planted out 3 ft, your shrubs will almost be touching the wall in a few years. Planted closer - you will be running the hedge trimmer back there to get them off the house. I had to go all over my house last year and remove all the branches of everything that touched the house because carpenter ants had started crawling up under the siding. Create curved beds that can have walkways to the house, or through the bed around the house to the side or back yard. You could begin an evergreen shrub border anywhere from the end of the drive to partway up the drive, and S curve it across the lawn at a diagonal around the corner of the house. Make long sweeps, not short changes - it will make the property flow more. Do you have kids to think about play areas? Is there enough room in the back yard for their play areas? Do you need to keep the front lawn for a future badmitton or volleyball net? How much time do you really want to devote to garden maintenance? If you are inexperienced - you honestly do not know the answer to that question and I would suggest that you start small and see if this is something that you would enjoy spending free time doing. If you don't have time or prefer another hobby, its not going to be fun to have a bunch of deadheading, weeding, mulching etc to cope with to keep the front of your new home really nice looking. By the way the term perennials implies that they are less work because they come back every year. This is totally untrue and I'd say my perennials take maybe twice as much time as annuals with spring and fall clean up, deadheading, fertilizing, mulching, composting, pinching, weeding and the occasional need to divide them. I don't know where in zone 5 you are, but there are gorgeous evergreen azaleas, rhododendrons, pieris, boxwood, chamaecyparis, junipers, microbiota, cotoneaster, spruces, fothergilla, itea, witchhazel(15ft) and hollies just to name a few things that remain in the 2-5 ft range which would require minimal shaping from you and give you fantastic color. There is a new dwarf 10-12 ft white birch that would give you multiseason interest set off the corner of the house. If sited so it grows to its proper size, Taxus baccata repandens will begin to weep and is a very pretty shrub. There are lots and lots of plants to choose, but most designers will tell you to first design the shape of the beds and any hardscape like sidewalks, stepping stones, water, lighting. Then you sketch the shape and size of the plants you want. The effect I want is for someone to stand back and see a seamless home and landscape, where the landscape uplights the home. Think about layers also. I think sometimes white fences look really nice in front of white homes - also native stone and dark green ground covers. The final step is picking the plants that fit the criteria you've already established. If you are going to change the color of the house you might decide on that first because you wouldn't want to put together a foliage or flower color selection that didn't complement the house. Karin mentioned doing research - and I'd take that to the library and page through landscaping books and books of great gardens to look for ideas that appeal to you. You may end up having an all white garden like the Sackville-West famous garden at Sissinghurst Castle - most photographed garden in Europe. A great catalog to get on the mailing list or website just to look at the pictures is White Flower Farms. They always have awesome annual container combinations. Good luck and keep posting photos as you go along.

Check out this video by Rosalin Creasy, the queen of edible landscaping. She also has a Web site. Then follow any links from there. You'll find a lot of inspirational photos and resources online. Yaardvark's basic design can be followed, you just need to figure out edible plants with the shapes he has drawn that thrive in your zone. I'm not that up on edible weeping plants, but lots of big shrub-shaped edible fruits and there are also fruit trees that have a columnar shape (column shape) such as sentinel apple trees. Raspberries and blackberry tend to get droopy and weepy-ish shaped (fountain shaped). There are edible easy to maintain groundcovers too, like lingonberry, although they need acid soil to thrive so you may have to amend. I grew bearberry which also goes by the name kinnikinnick as a groundcover. It is not really "edible" so much as medicinal, where it goes by the name Uva ursi. Lots of herb ground covers like thyme and chamomile and some low growing mints. There's also wintergreen but that needs shade and can be fussy. Not too much in the way of edible evergreens although you can grow balsam or fraser fir in some zones and collect the needles for their scent and oil. With juniper you can harvest the berries and make gin. Some junipers are columnar. Some make good groundcover, a fairly common low maintenance option for small yards. Edited to add that you're going to have to be thoughtful about planting your front yard since most edible plants like sun or partial sun, and your sun is going to be filtered at best. Try not to plant things in the shade of other things, so watch where the shadows fall during a whole day at different times.

I've noticed that whatever size is printed on the tag or is claimed on the Internet, is about half of the real final size. In their desire to see quick results people are prone to getting fast growing plants that soon get out of bounds. I think it's better not to rush it as time seems to pass quickly as soon as one focusing on other things. With water and fertilizer I find most plants to grow reasonably fast. There are always exceptions but as a general rule, they do.