Update - I just had a roofing envelope person stop by to look at the house. He said the issue was (is) likely 80% related to condensation and 20% crappy roofing job in that area. He checked the whole roof and noted all vents are/were covered in snow, so the attic can't breathe properly causing condensation to run off in that area.
So not only do I need a roof fix in that valley, I also need 6 "max vents" on that side to ensure proper ventilation in the attic. They are taller and have multiple levels of ventilation and seem better than the basic/short caps I have up there right now. $130 each at Rona.
Anyway I was impressed someone could confidently say that was the cause of the water running down the side of the house - no one has been able to figure that out yet.
The downside is they are somewhat swamped with similar calls and the wait is 1-2 weeks.
Here's hoping it actually solves the issue!
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