i wish i had a dollar for every time i write this ... start by understanding.. that foundation plantings.. are planted TO HIDE THE FOUNDATION .... not 'ON' THE FOUNDATION ... of most importance to me.. is to leave 2 to 3 feet at the foundation to walk ... for xmas lights.. window washing.. ladders ... maintenance.. etc ... so i would start by building some nice foundation beds .... on the left ... by the steps ... the garage.. i would build a wall ... to make a leave bed ... its not hard.. but it needs to be done properly .... and in that bed.. i would go with perennials .... nothing big ... just a selection of plants that will give some flower interest all summer and fall ... is there a man or a burly son available.. to move retaining wall bricks ... its not that you cant do it.. but it can get heavy ... [after messing with your pic.. i dont know about the wall.. lol] .. its hard to grow things on a steep hill.. one solution is the retaining wall and leveling it all .. but that might be a long term plan i would then put a minimum 3 to 4 foot bed on the outside of the sidewalk ... and go all the way around the front of the house ... but not a straight line ... and then i would go 20 to 30 feet out in the lawn.. and look for some trees or shrubs.. to lend a vertical to it all i am not familiar with the 'new england look' ... so be this what it may ... use your money to build good beds.. and get a few of the bigger plants in ... and fill in with some annuals for this year ... and consider the rest your new 'hobby' .. lol ... check out the link for how to do the beds .. and use the search function above for 'building new beds' .. or some such thing ... your worst mistake IMHO .. is to think that this has to be all done this year.. and only with that budget ... build the backbones.. and the rest will follow ... gardening is a lifetime thing.. and usually not instant gratification ... [and i bet those are the landscapes you are not liking in the area ... unlimited budget.. and had to be done all at once ...] and just cruise the 'hood' .. and steal ideas ... lol .. and see if you can differentiate between those peeps who jammed it all right on the foundation.. and those that have used the area ... as i tried to describe above ... i bet the ones you dislike.. were perfect the day they were planted.. but those darn plants just keep growing.. and all of a sudden.. it looks like the jungle is trying to swallow the house ... [in fact .. take pix of the ones you dont like.. and post them here.. and we might be able to tell you why you dont like them .. its a back door to figure out what you do like] after the backbones.. and the beds.. i just collect thing i like.. i dont really care what others think.. nor how 'professionals' [and i use the term lightly] ... would do it ... its my castle.. its my realm .. and i am the king .. and if you dont like.. bite me.. lol [actually my boy did once.. dont say that to a 3 year old.. lol] my bottom line.. i just wanted to get your head out of that small space between the walkway and the porch.. and make you understand you have a big ugly lawn out there.. use it ... who needs grass to mow ... ken ps: we can work on the back of the house next year.. and the side in 3 years ... as the budget allows ... dont spread yourself too thin.. do it right the first time ... and dont look back ... in fact.. with $1000 bucks .. we can build the beds all around the house.. and get some backbone large plants in real easy.. if you can do the labor yourself ... i am hitting send .... cuz this thing may never end.. lol .. Here is a link that might be useful: link

I was looking at your photo and thinking, "Oh, white gaura. One of my favorites!". And then I read you want to yank it out. lol I let mine reseed, then spread them throughout the garden. The seedlings don't start off all that quickly, so they are easy to pull if they come up in the wrong place. It looks nice--not bare at all. Give it 10 minutes. ;) The phormium might get too big being so close to the walk. I would scoot that one back a little bit so you don't have to cut the leaves off all the time. You do have a lot of plants in there already. That is fine, just keep in mind that you may have to remove some of them when they get rolling/growing.

It is difficult from these photos of smaller areas for me to figure out how it all fits together and get a feel for your yard. It would be most useful if you chose one part of the yard such as the front and took one set of photos of that part from something of a distance that spans the whole width of the yard from the neighbors' homes on the side and includes your house. The easiest way to do this is to take one photo from across the street and then stand about 20 feet from the house, opposite the center of the house and pivot your body to take a set of photos that go from one property line to the other. You have to include the house since it's a big part of the overall property. I can assume from what shows of your neighbors' homes that yours is two story with a second story deck on the back, but I can't really tell where the photos are on the property and how they relate to the building. As an example, here is a thread with a set of photos that are really helpful. [https://www.houzz.com/discussions/need-design-help-replacing-rock-mulch-and-plants-dsvw-vd~4574536?n=33[(https://www.houzz.com/discussions/need-design-help-replacing-rock-mulch-and-plants-dsvw-vd~4574536?n=33) In the first photo, there is a good overview from a distance, and in the original poster's first follow up comment there is a good set of photos all taken from the same spot. They overlap a bit more than needed, so you could do the same in fewer photos, but they give a great idea of what is there now, location of trees, beds, etc, and how they relate to the building, walkway, etc. If you aren't comfortable posting photos of the house, add a photo of a measured drawing. The plot plan would be a good start, bit then you need to add the location of anything not on the plan such as your front yard tree, any pavement not shown, etc. I would definitely remove the rocks around the tree and the grass immediately around the trunk and a few feet out and put down a shallow donut of mulch, being careful not to let the mulch go against the tree trunk.

One thing comes to mind right away - small and sharp curves (next to the stairs) are going to be a PITA to mow and trim. Do large and gradual swoops instead. Don’t make your work harder. Pretty house.