Here are some pics

Pic1: where cantilever will go to make even with the kitchen and add slider
Pic2: back of the house where back door /stoop currently are

I think I would replace the stoop with a deck, the width of the house bump-out, and the depth of the existing patio. That gives you a spot for the grill, and a chair for a morning cup of coffee.

Perhaps steps to the patio area could run the depth of the deck. It's low enough that it shouldn't need a railing. Expand the patio as much as you need for the use you desire. A pergola might look great, depending on the direction the back yard faces.

Thanks. It’s about eight feet in depth and probably increases cost by 5k. Might be worth it though.

Initially wife didn’t love the idea of a deck but I think it makes the most sense.

The plan is to cantilever where the bay window is and put a slider to serve as the man exit/entry to back yard but having two stoops seems silly.

Can you close off the current entry to the back, and you'd only have the one stoop.

I actually like two stoops, with plantings between, patio pulled out into the yard (assuming there is room) to allow planting close to the house. (That would require removing some concrete, though.) The patio could be sheltered by a pergola eventually if shade is needed, and it could have more plantings developed around it.

Looks really nice. My contractor also suggested a planter in between.

I will share this with him as well.

Thanks!