Thanks to all for the good suggestions! Current state of the project area: The former herb garden along the east edge of the yard behind the house has been dismantled! All of the often used herbs (oregano, parsley, cilantro, basil, thyme, rosemary) have been moved to the small bed just west of the back door. This will end up being a pretty densely vegetated bed, but that usually helps keep down the weeds. :) Slipped a few flat stepping stones between the plants for ease of harvesting. I love it! No need to even put on shoes to get fresh herbs! Chives are in front of the (not often used) air conditioner unit. Some of the bigger herbs (lavender and sage) are a little further away--just past the a/c, but making a nice little border connecting all of the herbs together. Some of the other herby plants (hyssop, rue) have gotten moved into other spots around the yard. Now that the herbs are relocated, I've spent a lot of time staring at that area between the back of the house and garage. We do want to make this into a patio area, flagstone (with creeping groundcover and smaller stone in the gaps), with the BBQ grill closer to the garage along the fenceline. One of the remaining issues with this area is the need to adjust the grade. Currently, the level of soil next to pond and under the flagstones from the back door to the garage is slightly elevated--which impedes water from draining quickly away from the foundation. Luckily, the elevation drops again near the fenceline, and definitely sloping down to the narrow section next to the garage and into the alley. This will definitely be a big project, removing the right amount of dirt and leveling it. It also has the additional issue of being infested with bindweed, so I'll actually need to get rid of this dirt entirely (for which I don't yet have a good strategy). Plus the expense of a large amount of flagstone. The other issue, which I haven't mentioned before--is the wretched state of the neighbors privacy fence all along this east edge of the yard. It's definitely falling to bits at this point, but I'm fairly certain that it's repair or replacement isn't high on their list. Sigh. All that being said, it looks like the narrow section path of the yard may again be shelved for another year. But small strides are being made. I've moved the shrubs from the back corner of the house to better spots. I'll probably continue with rearranging the current plants in this area this year, in preparation for finishing up the stepping stones and groundcover here next year--hopefully! I love the idea of some sort of arch/gateway towards the front of the path area, which will help break up the very tall and narrow aspect. Maybe also a bench near the porch, to make this part of the yard more visiting friendly. thanks again, and if there's any more comments suggestions...especially about any good tricks for aiding with the grade/drainage and getting rid of "bad" dirt...

The plan and sketchup perspective are helpful. It was the deck along the side that I wanted to know about. If you limit the width of the swale to only about 4', you may not be able to achieve enough capacity to hold all the water during a torrential storm. I'd widen the swale to about half the distance between house and fence. Making it wider is fine, but the wider it is, the larger the retaining wall must be. Though I said I'd avoid creating the swale below the deck, I will now eat my words. Often, in a remodel situation--especially with limited space and where everything around is already built up--one cannot do everything in the perfectly ideal manner. But in creating it under the deck, I'd make sure it's wide enough to have sufficient capacity. In the sketch, I'm showing the deck using the wall as a support, but whether you could do that, or not, depends on how things shake out in the relationship of finish floor elevation (ffe) to existing grade. You seem like the kind of guy who would have a nice laser level, or need an excuse to buy one. You might some evening use one to mark the ffe directly on the grade (with paint) so you can get a nice visual of what you're dealing with. Depending, you may be able to create a secondary swale at the top of the wall and disperse the water before it goes into the primary swale. But because of grade and roots, that might not work out. You also might build the wall higher than I show and connect the deck to its side. Or, the deck may be independent of the the wall. Hopefully, you can understand the sketch of the drainage scheme. The arrows indicate that you must drain water away from your house at ALL sides. Near the back, it collects in the swale and is moved around the house to lower elevations on its way toward the front. I would not be much concerned about the tree roots. The prior disturbances are long ago and trees have nothing better to do than grow replacement roots, so they've long ago been re-established. The rear-most tree will maintain more than 3/4 of it's roots in spite of your building a wall in its vicinity. Near the front-most tree, if you end the wall aiming directly at the trunk, as I've shown, you will have little need to remove many large roots. It can recover from other excavation you do in the vicinity. (See the part of the sketch, in red and black, floating above the deck.)

I am unclear as to your question. Are you looking for general ways to turn it into garden space? Is water an issue? This is an entryway designed by Michele Derviss, a San Francisco area designer. The house is just visible in the upper right side of the photo, and the main entry is the middle of the left side opposite the stairs. If water is an issue, you could make the path that parallels the front of the house permeable with a drain under it that diverts water away from the front of the house by channeling it over toward the side. Here are couple of other ones from the same designer: Notice on this next one the center drain in the patio and how the patio slopes toward the drain:

Doug, wow! Your illustration is so detailed and helps to give me a better idea of how to add some depth and dimension in the front. I'm really keen on the symmetry of your first sketch, with what I believe to be liriope? I honestly never thought about extending the retaining wall to the front elevation or adding steps. Thanks for taking the time to sketch up those concepts. This is likely the direction we will go as the stone from the existing retaining wall is also used for the pathway the leads from the driveway to the back patio and around the entire back of the house. In evaluating ground cover, Pachysandra is one I seemed to have overlooked. We have two huge maple trees at the very bottom of the front yard and don't want to plant anything that will pose a threat to them. Great suggestion there. What is a reasonable range to expect for a project of this scope? I understand every region and professional is different, among many other countless factors. Just wondering if this is $8k-$10k vs. $15k-$20k job.