It strikes me that this is a property that would benefit from strong lines to add a bit of symetry and give the 'negative space' a stronger presence. Any chance you could move the foot gate to the right so you could have a straight path entering that then splits with the path going left to your house and right to the other one? Granny's garden would be on the right and you could make a matching one on the left. I tried to draw it on a copy of your first plan, but it didn't come out too clear on this scan:
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I'd move the veggie area to the sandbox area if you could to make the center area with the orchard as simple a space as possible - just grass and the trees (with the seating area at the front).

With the 'ugly shed' gone, that would give you space to expand the compost area and I'd shape that whole area to mirror the trampoline area on the other side.

I played around with 'painting' your work shed in the style I did for our shed this summer - i.e. paint the trim a lighter shade of the body color and the doors a darker shade. (The window sash/muntin bars should probably be dark too.) I think it would make the shed a better background than it is at the moment.

I'd be inclined to keep all the path materials the same. I prefer ramps/slopes to steps - but that reflects my personal needs.

A possible repainting of your workspace:
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I can't open other pics,only a suggest:
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Hi Woody-
Strong lines - yes, but their placement needs pondering. In the recent thread about curves, I mentioned the straight line that hurt my eye; you can see the line in the "before" picture on the lower right. Possible explanations why it bothers me are: 1) it runs too close to tree trunks, 2) it disagrees with the contours of the slope, 3) it points at my kitchen window. In earlier drawings I tried to shape the path from door to car like a very stretched-out "s" but it looked sort of weak that way. Here, I just moved the line away from tree trunks. Another unhappy line is the long diagonal - it looks like it needs another diagonal for a friend. It used to lead from House 2 to the well, but the well isn't there anymore. The area around the foot gate is one where "nothing will grow" due to tree roots, so the entrance is not as welcoming as I would like.
Quite a bold take on relocating the foot gate, and one I haven't considered. Granny would never let me have that, but in theory, it would offer a solution to two problems mentioned above - the long, unhappy diagonal, and the unsightly entrance. On the minus side, it would increase the amount of paved surface in the yard (I'd still be keeping the old path, to get to the basement) and (maybe) spoil the view from the seating area.
Moving the veggies would be easier, and if I did, I'd probably also want a barrier of shrubs between veggies and parking. Indeed, I once fantasized about a formal hedge on that line, extending to the central foot path, where it would form an arch - but clipping hedges is not really my favorite activity, so I've given up on that.
I've questioned the shed's color scheme myself (I'm testing on the shed before I paint the house), I'll live with it through winter and see. I chose the warm colors to cheer me up in November, but in summer, they start competing with flower colors.
Ideasshare, I took a mental walk in your painting, and had fun bumping into trees in the dark!

I love the deep burgundy color of the workshop - I just think it would look better if the trim and doors were in shades of the same color, rather than pale colors. I think the burgundy color makes a great backdrop to plants, flowering or otherwise! Would Granny let you encroach on her garden to make the move of the footgate possible if you sold the idea as expending the garden to include the other side and enlist her help choosing the plants to go there? The seating area then would face an expanded garden and be an extra-attractive place for Granny (and others) to sit and admire it!

I'm not sure which horizontal you're referring to as bothering you - is it the area where the numbers 49.21 and 49.23 are? Is that a driveway of some sort? Is the fence that the foot gate enters through a solid barrier? i.e. could that area become an enclosed courtyard or is it sloped too much for practical use? With my 'Y' pathway with the moved footgate, I assumed that the basement entrance path would remain much as it is now between the front door and the basement entrance, shaping the garden matching Granny's to fit the paths and the hardscape(?) adjacent to the outer fence. I think access to the basement from the 'courtyard' area wouldn't be much affected/need additional hardscape.

I am not a big fan of clipped hedges - at least not if I have to do the clipping! I use 'Pink Beauty' potentilla as a sort of informal hedge in a couple of places - it stays small, blooms not-stop all season and only needs 1/3 of the stems removed at ground level each spring to keep it a nice neat mound. Dwarf Korean lilac is a bit bigger but also stays a reasonably small neat shape with little work. Perhaps something like those could be used as an informal hedge between the cark park area and the rest of the space.

I think your view from the second story would look fabulous with strong geometrical lines through a largely green midground, with a Y entrance pathway directing foot traffic through the flower garden.

What I'm 'seeing' when I picture the changes I'm proposing is my maternal grandparents' farm where I grew up. There was a short driveway off the road. That connected to a substantial racetrack-shaped driveway. The house, barns and garage were arranged around the 'track'. Movement between building was easy, either by foot or by vehicle and, at the center of it all, was the calm sea of green. It was a powerful mix of strong 'formal' lines and weathered wooden buildings. It still shapes my perception of a landscape that says 'home'. Your landscape with the overtones of multi-generational family on one property 'speaks' to me in the same way.

The straight line in question was in the photo, and it's the little raised edge bordering the orchard.
Here's a view of the South part from above:
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View towards foot gate - the shrub in the middle got a hard pruning this year, but it's usually three times bigger:
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Winter panorama:
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So here's how it turned out: half of the hardscape is completed. The northern half will have to wait till spring.
I chose a continuous slope instead of steps (both options had their drawbacks, but in the end, stumbling on the stairs in the dark seemed like a bigger inconvenience).
The circular patio will be covered with treated wood.
I will probably continue with a little staircase leading from the circle to the diagonal path (weather permitting), but first, I need to stop erosion by laying down bits of turf. DH is re-doing the steps at the front door.
Pictures:
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I think you made the right choice about the continuous slope.

Please compliment the workmen for me: it's lovely.

Thanks, I'll compliment them for you.
This project has shown me I'm challenged when dealing with a three-dimensional space (a flat lot would be so much easier.) The other hard thing, for me, is plant removal. I did take out a row of roses parallel to the house wall, this side of the paved path: they didn't bloom and they suckered. There are still two rows of shrubs waiting to be removed (visible in the middle of the last photo - bordering the path where it begins to go uphill towards shed) - what's your verdict on those?

About the shrub removal: I'm glad that's a decision I don't have to make. I like the shrubs as a backdrop to that bit of flower garden (irises?). And I like seeing that bit of garden from the front gate (in the first of today's photos).

But on the other hand, removing the shrubs would open up that area. And removing the flowers as well and planting grass would change things even more so.

I'll chicken out and say I don't know enough to make a decision. And that's true: if it were my yard, I'd wander around and stare at it from different directions for a few years. 8-)

How would you feel about renovating that corner garden, perhaps with new shrubs? The best of both worlds....

Oh, I have stared at the garden long enough to grow used to they way things are!
Perhaps I should have mentioned the problems with the shrubs: the lilacs, left of the path, sit on top of a retaining wall that is slowly disintegrating. Also, they make a solid wall along the terrace, so this part is more open to the street than to the rest of the garden.
There are 4 young pines on the terrace, which might become a new backdrop, if they don't lose their lower branches too soon (one black pine, 3 scots) and a Rosa Glauca between them, in the corner by the car gate.
The rose bushes, to the right of the path, have a bug that eats the flowers before they open. If there was an organic remedy, I'd give the roses a chance.
I'd really like to add some shrubs with good fall color, but they'd have to be tolerant of sandy, slightly alkaline soil, and not have toxic berries.

Update: I'm not so sure about putting the car on a raised podium any more. It is also still unclear if and when the &%(â¬#;;) green wagon is going away. I'm thinking of going the easy way and continuing the brick path to the shed door, and doing the parking area in limestone (not turfstone). The first pic shows where I stopped last fall, the second is one possible way to continue (compare with pics above) with the trim and door coors slightly modified, and the third is just a musing on how the shed would look with black trim. Here goes:

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Ideas welcome if they don't include broccoli or roses.

I think it makes sense to continue the path to the door - unless you would be parking vehicles on it. Would the path material hold up under the weight of parked cars?

I like the darker trim - but I'd go with a darker shade of the shed color rather than black. And that white window frame needs to be darker (the color of the shed?) so it doesn't glare out at you so much.

Has spring arrived in your part of the world? I'm waiting impatiently for things to warm up to working-outside temperatures here. Still some snow on the ground and we had a minor snowstorm (6-8") last week. But there are a few crocuses in bloom now, so spring is starting to happen....

Would it make for easier access to the shed if you started to step down from where the path ends now? You could go down to the shed level immediately and have a free space in front of the shed or go down, first to a landing and then on down. You could plant giant cauliflower on the slope and paint the shed trim to match!

Ink, the slope goes up not down... unless you're kidding again and I'm not gettin' it. See that you got a basket of vegetables prepared, is a rotten tomato among them?
Hi Woody -
We had the first rain of the year two days ago (can you tell I'm excited): we spent yesterday cutting trenches in ice and floating wine corks in streams. The snow piles are still big enough for digging caves. Nothing blooming yet but definitely not winter any more.

Still sounds pretty wintery to me! Here's sonme 'Cream Beauty' (my favorite crocus) for you...
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When do the early bulbs appear there? We've had snowdrops for a few weeks; Heleborus niger was blooming last week and the crocuses are coming on now. Tulip and daffodil foliage is showing in various states but won't be in bloom for another few weeks.

Yeah! for spring at last...!

I only use the word 'down' four times timbu so strike them through and change to 'up': problem solved. I must get my eyes tested because this explains why I fall up the stairs that most people fall down.

Look what I just found! Wasn't there yesterday so must have been growing under snow.
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Some "after" photos - "in-between" photos to be more precise, since I still have more than one loose end to tie -

May 2. Just took down the big lilac from the corner of retaining wall. Patching the pavement and lawn next to the brick:
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May 6. The path has reached the shed.
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May 14. Half of the wall rebuilt; one Microbiota and one Weigela planted, creeping sedum planted on other side of path:
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Looking down from the terrrace, same day
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June 12. View from the door with serious flower porn in sight:
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July 1. Things have grown a bit. 2 mini mugo pines planted in the corner near parking lot. Ignore the blue lobelias.
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Sweet!

You really made all the correct decisions.The curve of the walk as it approaches the shed is just right. And by using the limestone pavement to either side of it (rather than branching the brick walk away from the shed), the shed is more of a visual destination.

I like the limestone edging along the right side of the brick walk. (Wish I could do that, but the Bermuda grass would grow right though it ... and over it....)

To sum up: it's all very clean and neat. You tamed the garden-overtaken-by-time, but without losing the naturalness.

===

White fuchsias! Are they hardy in your zone? What cultivar are they?

Truly stunning timbu, stunning, see what happens when you ignore my advice.

Looks great! I particularly like the circle with the table, and the stone wall - I love stone walls... Are the shiny bricks slippery? You don't see ones like that around here - they almost look more like tiles than bricks. Are they a commonly used material there?

that is really beautiful. I really love the formality of the brick walk contrasted with the irregularly shape patio stone and edging. What a great example of how structure adds/tames a garden!

Missing - the fuchsias are in pots, and are definitely annuals. Variety unknown.
Woody - these are clay bricks fired at extra high temperature to make them weather-resistant. They used to be imported from Germany, but are produced here since last year (which dropped the price by half, but the local ones only come in two varieties, I really hope these will age gracefully and take on darker shades... in 200 years time, maybe?) Not slippery so far, were covered in snow in winter anyway.
Drtyrl - the reasoning behind using different materials was that I had quite large areas to pave, and was afraid of a big uniform surface, so had to break it up into smaller parts: brick for "fast" paths used frequently, limestone for "slow" secondary paths and walls, wood for sitting down and relaxing.
I like that I can step out in slippers now, and have less lawn to mow. Granny's reaction was: "This is too posh for our place!" (well, she had the same reaction when a bathroom was built to replace the dry toilet) but she does appreciate the ease of moving around. DH and my dad (and of course you too) helped me make many of the tough decisions - encouraging me when I felt it was all going to hell - and son, as I already mentioned, is using the path in ways I'd never have thought of.
I need to build one more retaining wall - now trying to figure out its shape and location - for the ground was raised near the shed door so the parking could be level, and there's a knee high change in grade towards the veggie patch. The other area to think about is the lower entrance from the foot gate.
Thanks for the kind words so far!

When I saw those first pictures I thought you wouldn't be able to do it. Then I saw the pictures of your yard under construction. Still, I didn't think you could pull it off. Too many irons in the fire and nothing completed. Just a big mess.
...and then,...Viola!
You pulled it off!
Congratulations.
Mike

Mike, I've heard those words before and on occasions far removed from gardening! Looks like I always have to pass through a stage of hopeless chaos whether I paint or cook... what's the diagnosis for that?

I liked the quaint chaos of your former yard, and I love your "posh" new updated yard. You did a beautiful job! It was hard for me to picture the updates from the Photoshopped pictures, but everything came together beautifully. I also love the character and colors of your homes and shed. Thanks for sharing all the pictures.