

Help me with a last gasp attempt to address chimney issues
I have had issues with water coming in around my center roof chimney since I moved in 5 years ago (house is 90 years old). Only happens during heavy, driving rain.
I was first told “has to be the flashing“ and did the whole roof (with new flashing obviously). Did not fix it.
I was then told the chimney was in real bad shape/water logged. Rather than doing a bunch of repointing and repairs - I had it rebuilt roofline up (new crown, cap etc.). Did not fix it.
I’ve taken to climbing into the attic during heavy rain and watching. What it looks like is water emerging FROM the original old brick below roofline repairs and NOT water running down the brick from behind the flashing (although it’s tight up there and hard to get a great look). Pic below.
So my question is 1.) is that a possibility? That the new brick becomes saturated and water runs down to the old nasty brick, finding its way out?
And 2.) what to do? I think I’m down to two options: stucco which I’m really hesitant to do (live in MA, doesn’t address structural problems) or just tear it down and roof over it.
I have a hard time believing it’s the flashing as this problem has transcended 3 different sets (original, roofers and masons). But the mason has been willing to help and I have a 3 year warranty- so if you guys say it isn’t the brick, I will go back to them.
A genuine thank you. I need to get this figured out.
Edit: here are some exterior photos