If I felt certain of anything, it would be how undesirable that hedge surrounding the patio is, unless one wanted to separate themselves from the rest of the yard. In addition it adds to the difficulty of seeing the yard so it's hard for anyone out here in cyberland to understand just what IS there.

Another things that is pretty much certain to make the demolition list is the wavy brick bed edging. There's no reason for those waves so they seem like a busy distraction, and the bed they create is far to shallow (front to back) to actually have anything growing in it. It should go away.

It looks like there's some kind of hedge opposite the patio doors. Those shrubs can't like the extra shade created by the low hanging tree limbs.

For every photo you've posted, I find myself wondering what is to the left and right of what is shown. If you add any pictures in the future, please pivot the camera, taking slightly overlapping photos, and show the wide scene. Then we can understand how things relate to one another and fit together.

All good points and feedback !! Hope these additional photographs help a little.

I'm leaning towards -
- getting rid of the pergola,
- remove all shrubs and plants along the fence.
- Re-do the flooring (brick or stone)
- maybe a large seating + bbq + water feature? where the current pergola is
- Have a small grass area in the existing smaller section or extend the floor there.
- not sure what to do in the large open space....should the putting green and a grass area be there ?

Is this a DIY project, or you'll be having the work done? What kind of budget are you estimating?

Sorry, the new photos cannot be combined into a single, wide scene, which not only makes it more difficult to understand your property, but eliminates a possible way of giving feedback to you.

You didn't say anything about the shrubs surrounding the patio. If you're going to remove them, it would be good to do before you take the pictures. That way we could see things.

@Yardvaark, I will hire a crew to do the actual work :) It's the design and the many possibilities in this huge space is what I hope to get some guidance on.

I appreciate all your input.

Why would you get rid of the pergola?? Also think hard about tearing out the established shrubs in front of the fence. Just limb up the trees above them, as Yard suggests. It takes years and much water to get plants to the size you have. Until you're sure they are not contributing features, wait. The hedge around the pergola is probably an obstruction and could go. Straighten out the brick edging.