"Anyone want to take a crack at how to make it all work?"

Whats there now? How can anyone know what or how to add on without this info? Is the current structure and foundation structurally ok and string enough to add up?

What Summit said.

Thanks CP. I realize what I said could be read as snarky. It's not meant that way. I'm currently working on two houses that have each been remodeled at least three times. Both owners are going to have to spend huge money to finally get it right.

Good advice Summit - my husband has provided quite well for us and a large part of his business has also been fixing what others have screwed up.

The sketch posted by the OP is basically a square...the fattest of all plan shapes, which will be darkest on the interior with the least amount of natural light, and will have the largest, out of proportion roof.

It's probably the worst beginning point...