Haha ,mine setup is similar. I got uninsulated ceiling above my fireplace . AND... There is a floor register above it with 4 feet 6" duct that not connected to anything . Lot of room for creativity .This is a great thread. Your situation sounds similiar to mine. I run a quadrafire 3100 insert upstairs it does an adequate job of heating the upstairs. Not great but ok enough.
I've got a partially finished basement with a walk out. No fireplace but a hearth area where you can put a wood stove. And a connection into the 2nd flue from this area
I thought about the same things your thinking about. However I'm never downstairs so I need something with very long burn times in the basement. I'm thinking a cat stove ?
Also there's a forced hot air heating duct that runs right above where the wood stove would go. Do you think if I cut an opening in the air duct and put a register there, the heat from the basement stove will naturally fill my furnace air ducts enough to make it's way to the upstairs and out the registers ?