Since the Stages sinks have integrated cutting boards and prep accessories, I think it will be functional in the island, especially if you can make the island longer. It occurred to me that if you can move the entry as far to the right as possible, you could have a more direct route from back door to kitchen, and separate the clean-up and prep/cooking zones, while still having a secondary prep zone on the end of the island, convenient to water at the clean-up sink. This plan would also eliminate the blind corner, and leave room for the second oven. If you decide on the smart oven, it and a MW (or is it a combo?) could be located just inside the entry. (See alternate plan.) The drawback would be that the walk to the pantry is a little farther from the primary prep zone. Can you cut back or remove the jog at the end of the hallway wall? That would give you a more space for the range wall. Alternately, you could have a shared trash pull-out on the corner by the range, and have a MW drawer across from the fridge. If you don't opt for the second oven beside the entry, there will be room for an extra prep zone beside the clean-up sink.

@BethYes, I saw some of these before and afters when researching and they give me hope! I will try to mockup wood paneling over the garage like you suggested. I love the garage door style, it is actually what we have in mind but could not reproduce in the mockup tool I am using. Also, your fence suggestions have given me some inspiration ... perhaps I could try to paint or stain the concrete wall black to tie in with the black timber retainers suggested by @hallettco and then try to use some pattern of wood panels over the concrete wall instead of a full wall of wood. I will play around with that idea and see how it looks.

@Sabrina Alfin Thank you for responding! I am trying to show him what I like and provide suggestions so I don't waste his time. He provided his ideas based off our conversation and I am not wowed yet. I have lots of photos that I like but the remodel would consist of taking the entire second story off. I was hoping to get some ideas like " add a second dormer, change the roof line.." so I can share those thoughts with him. I am a very visual person. I appreciate your time!

Nice place; great potential. Have you consider creating at least one short (<4') retaining wall to create a level place directly in front of the left wing of the house? Could it be done in a way to create a need for less steps from your front porch? Otherwise ... Because I am prejudiced in favor of usable porches. I 'd want to start at the chimney and create an 8' deep deck over the garage entry and wrapping all the way around to the left front corner of the right wing of the house and then continue the same floor level all the way to the left corner of the left wing of the house with a shed roof front porch roof with a forward facing gable over the entry door above the top of your front steps You could always add a roof over the deck later, extending the porch roof over the entry. Put a hip corner in the porch roof on that left side.. Consider having the left side of the porch even extend beyond that left corner of the house by 4' or even 8' and wrap around the corner enabling you to easily add steps toward the back yard -- or even a wheelchair./baby carriage ramp aimed at the back of the yard if this is to be your forever home. I would definitely NOT cut/scar the front yard with a sidewalk straight forward across/thru the front of the yard. I'd begin the landscaping by leveling a place along side the driveway beginning at the garage all the way to the road and put a sidewalk there. I'd add a retaining wall above the sidewalk -- taller (4' or so) near the garage -- and where I transitioned from the taller retaining wall to a shorter retaining wall on the road side of the lot, I'd have the sidewalk create a "C" curve from the beside-the-driveway sidewalk to the front porch steps, with NO steps in that sidewalk. Between the "C" sidewalk leading to the porch and the road, you'd only need a shorter retaining wall above the sidewalk to keep the dirt off the sidewalk. You could curve it just before you get to the road to create a level walk space behind your mailbox and create a planting area as the wall ends. Even if you don't extend the porch/deck around the right three story part of the house, the rest of the above should work. If you do add that extended porch/deck, you could also add steps leading to it from the driveway/garage with the steps aimed at the back yard from the deck/porch beside the chimney.