All sorts of issues, updated with PICS

Casey, you have a similar situation that I had when I joined the site a little over a year ago.

First home, extremely weird and pretty dangerous set up. I had a small stove that actually punctured the back of my chimney and wasn't safely lined to the roof, which you'll probably find out today considering the smoke you found when you were on the roof. If the chimney is structurally sound, a 6" stainless flexible liner should be able to make it to the roof. When I bought mine, I bought the thickest flexible liner I could find and the insulation to help with the draft, which you seem to be having a problem with.

My recommendation would be to start searching craigslist daily when you wake up, at lunch, and after dinner in search of a new stove. Give it a few weeks and you'll find someone who upgraded to propane or natural gas that is just looking to get rid of a nice stove for cheap. They go really fast, so make a schedule of searching regularly. (I did the same thing for my splitter). Buy the liner, probably like $800 for a good one (not sure on the price, mine was like $500 total to go like 15', I only have a single floor ranch) and you would only be using the chimney as an easy way to get the flue to the roof.

See the attached pictures. I bought the Regency for like $300 and the liner for $500. The full upgrade, installed was only like $600 after I bought the additional parts and sold the old stove to someone looking for a small one for their workshop.

With the people on here, you can do anything stove/flue/installation/burning/firewood/seasoning related. Really a great site.

Looks like that clay liner stops short of the top of the chimney, and the top two, maybe three course of brick are laid in on top the liner, or close to it and then mortared interior to finish it off.

If that clay liner runs all the way up/down that chimney, that would be good.

I'd pull that rectangular stovepipearatus off there and see if there's a thimble through the wall, or just what kind of wall pass through is there. I'd sure like to see a picture of that too! If it's a rectangular wall pass through, you may be able to use an approved stainless wall pass through and brick/mortar that in there. It depends on the amount of masonry that surrounds that current wall pass through (nearness of combustibles behind that brick on the wall) as to whether you could use a clay thimble and meet code.

If there's a thimble, and the chimney clay liner is sound, then you could pretty easy run a stainless liner down that chimney, insulate it, and be in business. You may have to do some work regarding that wall pass through.