Picture album of our funky chimney: https://imgur.com/a/JxMF6Nm We bought this old (1963) house about 4 years ago to live in and to slowly restore. Right off the bat, the inspector warned us this funky old ugly chimney was detaching from the house and could fall. As band-aid, we had some helical piers shoved under base of the chimney to prevent it from spontaneously tipping over, and had the roof flashing redone around the top. As we have had some time to really contemplate, we can see numerous issues. It looks like this chimney was added onto the house and not originally built with it. Even weirder, is that it looks like it was added AFTER this adjacent addition that you can see it butting up against. Otherwise, how the hell did they install the siding into that tight space? Shaking my head. (By the way, the interior brick hearth was built OVER THE BASEBOARDS. I'm sensing a pattern with this builder) The bricks are deteriorating, and covered in moss. There are places in between the addition and the chimney that look like the trap moisture. At some point the owner tried to seal up some of the cracking with copious amounts of caulking or sealant or something. We have never used it for burning wood or gas (we are using a "vent-free" system for supplemental warmth) , but recently we had a chimney sweep come inspect it and he told us it was in bad shape. Basically said it was a open cavity into our house for water, air, and pests. Advised me to seal the ash cleanout, which I did using liquid nails and a stainless steel plate. He suggested we use hi-temp mortor to seal cracks in the hearth cavity (don't know the correct term). He also told us to call a mason, which I will do, but first I wanted to post this here to get some feedback about what I should expect. I'm already assuming there is no hope in keeping this thing. The only value, I think, it offers us is that buyers like seeing chimneys. (I do!) But, this particular chimney seems like it's more trouble than it's worth. Should I just have it demo'd and the wall repaired? Is there any value in trying to save it? Is that even possible?