Here are some initial drawings for the addition.
Ground floor The as built is supposed to be outlined in blue, but it seems to not be strong enough. The area labeled "As built basement" is the existing part. Down is towards the street (west).
The area labeled "ledge" is an offset in case I can't dig right next to the house. The basement height is about 6 feet (to the beams), but the lower level addition height should be about 8 feet. Since I am putting a bathroom in the hallway, I am assuming the bathroom height should be 8'. I'm not sure I can go down 2' right next to the house, so I put in a 2' offset. This may change, e.g. I may move the bathroom into the room & make the hallway narrower, or the bathroom could be shorter or perhaps the ground height can be lower.
The room may be a bedroom at some point, but I didn't label it as such.
The stairs go into a hallway which is in what is now the side yard. There is a door to the garage, but it got lost somewhere. It will come back. The odd red marks are because the software puts openings in walls if there are openings in the walls above, which is strange & annoying.
Main floor The part labeled "Inside deck" is the roof of the hallway below. It is open to the sky, except for perhaps a transparent roof, which is not required to be watertight (thus, the watertight requirement is on the deck surface). There wasn't comfortable room to put a door from the hallway to the deck, so I left it out. When I modify the existing house, I will (perhaps) put a sliding door from the kitchen to this area also. The hallway portion comes a ways down towards the front of the house so the door to the kitchen & the back door don't collide.
I will probably use the room to the left as a bedroom.
Top floor The as built part is the current dormers, etc, which don't touch the new part. The part labeled "Deck" is the roof of the main part of the addition. The part labeled "Tower" is the stairs up to the deck, stacked with the stairs to the basement. The area between is designed to give a place for the roof of the main floor hallway to slide under the existing roofline. The existing roofline doesn't follow the blue line (the inside walls), but the contour of the lower floor, so there is less space between the tower and the roof than it appears.