I don't usually feel competent to comment on layout threads, but I'll try this one as I see a couple of issues.

Could you switch the range and the fridge? That would allow people coming in from outside or through the house to get to the fridge and be out of your prep and cooking area. Right now, folks coming in from backyard or through the house has to walk by you or DH as you prep and cook to get to the ice and drinks in the fridge. That could be annoying.

You could maybe put a pull out pantry on one side of the fridge and a snack center on the other, which would also be out of the way of the prep and cooking zones. I know you said you don't need a snack center but you will as DS grows up and learns to make his own snacks and lunches for school. Also, DS may eventually have LOTS of hungry friends who like to visit and eat your food-mine certainly does, and this "snack center" can act as a sort of dedicated area for snacks that don't need cooking (cereal, bread for sandwich making, fruit bowl, lunch making supplies like brown bags, etc.), and it would be convenient to your island sink.

Also, putting the range on the wall might make it easier to vent outside(?).

I love the idea of the table height seating coming off your island. I have that arrangement and it works really well for us.

Finally, congratulations on your new house! I look froward to seeing it come together.

Quick note and then will think about it - a doorway from the outside deck with a DW door blocking the entrance into the kitchen and the range blocking the entrance into the rest of the house. You have blocked the entrances and put impediments in the traffic-ways.
SO - DW on the other side of the sink
- maybe swapping the fridge and range and make that new fridge wall a pantry storage wall.

You might as well cook in the middle of your nearest highway on-ramp.

This will require some thought. I don't think it is necessary to back a schoolbus into the dining room to improve the kitchen.

I would take out the door to the outside and move it down by the dining room. This will make it easier to access from the kitchen, dining and living rooms. Other than that, it's a nice plan :)

I'm trying to understand the layout on your print. When you walk in the main entry, what is all of that space to the right of the stairs (to the left of the living room)?

Am I reading correctly that the kitchen space is 11' 9 -1/4" wide?

Are you considering making the balance of the annex (after stealing what you want for the kitchen) into a mudroom and/or laundry room set up?

are the windows in the dining area counter height? and if not... can they be changed out to be counter height? Obviously I'm thinking along the lines of moving the kitchen into that area and putting your table by the deck.

Where is the back door now on your existing plan? Is it in the annex room?

Also in your new kitchen rendition, did you steal the annex AND the dining room also?

The main line of traffic through the entire home is past the range. It is not a nice plan.

Think about shifting the kitchen to the right. I'd keep the wall between the D/R and L/R on the right and open up the other side. There's lots of possible layouts if that general idea seems feasible to you.

I think the original kitchen is kind of sweet in a period way.

It's a bit tight by today's standards and the DW is on the wrong side, but essentially it was functional

I understand your desires for an expansive new kitchen but the traffic pattern and the immense 20 island would not make you happy in daily use.

Her island is not 20'feet long. It ends at the end of the stools. The continuing lines are drafting lines for measurements. Everything ends at the fridge. (see elevations)

Thanks for the thoughts and the questions. For writing such a long post, I sure didn't explain very well! Here's some more information about the house and lot.

None of the doors on this level go out to a yard. The house is on a steep grade, so the deck that's outside the living and dining area is at least 15' above grade and doesn't lead to a yard. The deck that's outside the Room Behind the Kitchen is like a catwalk that leads to the carport on the west. That deck will be used rarely - and mostly just to get to the grill that will be stored there. It might make more sense to call it a balcony instead of a deck, given how high off the ground it is and how small it is.

I'm leaving the dining room intact, but I didn't do a great job of drawing that. The kitchen dimensions are on top of the dining room, so it looks like the kitchen extends there too.

Sharonite - I'll try moving the range to the outside wall. I was trying for lots of windows, but a functional kitchen is more important than windows! It sounds like I've strayed far from a functional kitchen, but it's not too late to fix it.

Bflenton - I'll try the DW on the other side and try moving the fridge.

Lavendar - I'd love to put that door somewhere else - but it would be a pretty major deal to connect the two decks/balconies since they are so high off the ground. Let me play with that a bit once I'm on the computer that has the layout program.

Marcolo - So, uh, how do I get that schoolbus out of my kitchen?

Judydel - When I walk in the front door, I always turn to the right and head to the living room. The space on the right of the stairs is part of the living room, but the ceiling heights are different, so it feels a little like a separate space. The kitchen is about 11'-9 1/2 or 11'-10" wide, so there's an error in my string of dimensions.

The windows in the dining room come close to the floor. The ones on the east are sliders to the deck on the east. The deck is the pointy shape that shows on the existing layout. There is no back door in the existing plan, just sliders to the deck. With the cliff-like lot, there's a main entry door on this level and a sort of back door on the level below where there's also a family room, shop, laundry and two bedrooms. The bedrooms that we'll use are on the top floor.

Palimpsest - I had a soft spot for the old kitchen too. But, along with being small, the appliances didn't fully function and the cabinets were in bad shape. The previous owner had cut strange holes inside them and there was water damage. The realtor's photos skipped over those details. Why will I hate the long island? I could try a U-shape instead.

I'll be back later tonight after the 3-year old is asleep and will post some layouts that try to address the comments - Just wanted to respond now to thank everyone for the input and to try to clear up what the existing house/lot/decks look like.

All of the suggestions are greatly appreciated.

Sorry that I have so many more questions right now than feedback. I'm just intrigued by your space and trying to understand it : )

The "room" that is the entry from carport . . . what will that be? Is that a mudroom? And what is that other room in the front of the carport entrance room? Is that a bedroom? It looks like both of those rooms have closets and then it looks like there is a shared walk in closet. Is that right?

You show BIG ARROWS coming into the kitchen. But exactly where is the door leading into the kitchen from that side? What will the "walk in closet" be used for?

Mini, my main kitchen is long and narrow also. Have you seen it? It is a "U" shaped kitchen with a breakfast bar separating the kitchen from the dining area. And there is a small island. The breakfast bar helps to break up the bowling alley effect. Also, just so you realize, if you remove the wall between the kitchen and dining area, it will seem more like a breakfast nook and not an official separate dining room. Or maybe you can keep your separate dining room and instead create a dining nook to the left of the kitchen in the area you will be entering into from carport. It seems like you have a lot of room and a lot of options.

I was reading the dimension lines as part of the island so I see it is not quite as long as I thought.

I do see however that the door to the deck creates a traffic pattern right behind your back at the cooktop, and between your prep sink and range. I don't think you will like this. I would try to get those functions on one side of that traffic pattern.