Oh, and on a related note, any suggestions about what might be done with that hedge at the top of the hill would be great. It's currently intertwined with a sagging chain link fence, and I can't tell if the fence is holding the hedges up or vice versa. I am tempted to remove both, but my husband likes the privacy it lends to the front porch.

Bumping - any thoughts? The more I read about fall planting, the more I think i might be better off waiting until spring on this slope.

What's at the base of the rock wall? Sidewalk?

Tearing out the root structures that are anchoring the hillside might compromise the strength of that wall.

Is that wall contiguous with the two properties to either side of your house? If so, how do they have their sloped properties landscaped?

Working on a steep slope is a job for the experienced landscape renovation crew. For now, get an identification of the upper shrub hedge and leave it in place until you put together several quotes from recommended landscape professionals and work up a budget. Yes, early fall is the better time for plant installations. If you're brave, take a long handled strong metal tined rake and see what's hiding under the pile of burlap. Might be as simple as an old tree stump. But, a pile of anything on the ground is a haven for critters and the snakes they attract.

I had a similar front garden at our last house, and it, too, had a few nice shrubs along with a plethora of weeds. Fortunately, it had two narrow, horizontal paths that were virtually invisible from th sidewalk below but made it possible to garden without standing on a slope.
I had moved most of the shrubs (roses, hydrangeas, lavender, holodiscus, etc) from our old garden, so I had plenty of material to put in -- I just needed to clear out the weeds. I spent several weeks digging carefully so as not to disturb the good plants or the pathways, but in the end it was a huge success, all done on my own (no need to hire out). One bonus: I met all of our neighbors in the process.

Thank you! We love it so far - and yes, the sunsets are spectacular! We didn't end up moving in until the end of August, and there were so many other things to worry about that I just let the front slide and figured I'd worry about it in the spring! The photos above are from late last spring, and things have actually changed a bit over the last few months - the area looks much better in summer/fall, but there are some maple saplings that have sprung up and probably a number of other intruders as well. I will take some fresh photos this weekend to see what can still be IDed and think about what I might like to keep, but to be honest I'm not in love with most of it.