Tyler,
I've looked at your thread and what doesn't come clear to me is a cohesive feeling for your site. You have the sheep there -- why? Prairie garden where it is -- why? The answers for many things may very well be "because ___ was there already," but if item X that you visit everyday is somewhere inconvenient and item Y is something you check on once a week but is outside your front door, then what you may be need to do create new people patterns.
I'm not sure I'm being clear, so I'll give an example. The vast majority of my official "back yard" is taken up by septic lines. There's not really anything I can do about that, okay, so that's the "lawn" for the dogs and relaxation. And much of my site gets too much shade when it's not summer, so the annual vegetable garden could really only go in one place. This created a pattern where I went from my back door to the garden at least once a day. So I extended that pattern, with an orchard, then a shed, then planting on the back
fence, then a grouping on the other side, and next things you know I have a pattern where I make a circuit of the back
yard and look at the stuff that needs looking at more often, with a shed in a convenient location for when I need to grab a tool or something. A hammock in the spot where I can't grow anything. And some pretty stuff on the way to the garden to make it a nicer path (although I need to do much more work there). I started with something that had to be where it was, but the next step was recognizing my own pattern and how that garden placement affected everything else before I moved on to the next place for a
project, and so my site is growing more organically.
You have all these maps of contours and
water flow and such, but I don't see YOU. I would suggest that before you rearrange or add anything, that you spend some time observing yourself and your husband's patterns. Working with the
land patterns is important, too, of course, but I think maybe your vague -- discomfort? dissatisfaction? -- is a little discord between you and the site, and not any failing of your projects or ideas. Your hard work and enthusiasm shines through very brightly, and I am impressed at your efforts so far.