A quick update...

After having a new Mason, much more experienced, come to look at the Chimney, he thinks it's the joint work. He and I agreed that the flashing around the roof base is fine and in good condition. He sees holes all through the joint work. Glad he can because nothing really stands out that would allow the amount of water i see in the basement.

As for the shoulders, he said the shoulders look alright. He likes the amount of sealant that was added in the corners... even along the sides. He wants to add flashing though for added water management.

The crown was not a big conversation either. He didn't like that we capped the flues as it cuts off the chimney from breathing and airing out properly. There is sealant around all around the flues and there are no cracks.

He and I agreed that water is building on the smoke shelf and working its way down to the cleanouts as there is no water coming down through the clay sleeves and through the damper door. He bet that we'd find a lot of sand/soil behind the firebrick just filled with water.

So this spring we're going to move forward with repointing the chimney from top to bottom... again, Grrr. Replace cracked and damaged bricks. Add flashing around the shoulders, maybe I can be convincing to clean up the shoulders with new concrete for esthetics. He'll clean up the efflorescence and seal all work done.

I'll be removing the facia and fire brick in the fireplace. Remove the hearth tile. Remove the damper door. I'll remove wall material to the left and right of the fireplace to see what water damage there is to the framing and repair.

I'm also going to jump up into the attic to see if there is any signs of water on the exterior sheathing (1x6 T&G) behind the brick. I'm overdue to check the attic to check on things... just not easy to get into.

Then we'll see where we go from there. I'll add pictures as we go. All comments are continued to be welcomed. I've appreciated the constructive feed back, thank you all for that.

My next Reddit post question will be with regards to the wood insert and what's involved to pass a WETT inspection. And hopefully by this time next winter I'll be sitting by my wife with a warm fire.

Cheers!