Thanks for the advice @Owen Dashner @Peter MacKercher
I spoke with the owner, it was hard to get any words in. @Peter MacKercher , you nailed it when you stated "Remember, the seller is probably even more nervous than you are, so don't sweat it too much."
No numbers were given, only the history of the house and why it stands as is now.
However, most of the questions you listed, were answered with out any input from me.
The house has been in the family for a very long time. It became obvious that they are reluctant to sell it due to emotional attachments.
It was rented successfully for years when the family was there, occupying at least one floor. As soon as the last family member left, it all went down hill.
So it was left that neither of us are in a hurry, even though I really am if the price is right. I watched my father loose a great deal because "no one was in a hurry". Its a different story when someone walks in with a cash offer.
She will talk to the other owner and let me know what they think for a price. I offered to talk about anything from a straight purchase, to management of the property and open to any other discussion.
So I'm thinking I follow up shortly after the new year as the discussions with the other owner will not happen until then.
It seems they have some figuring out to do with the family right now.
As I'm writing, I realize I was actually a little discouraged to be dealing with so much emotion. Probably one of the benefits of working through an agent.