This is the moisture situation. There are two water stained areas on the soffit. A fair amount of water is getting through.
We took these pictures 9 days after the last rain, which was a very heavy rain (close to 2 inches). It was still dripping on the day we took the pictures.
The wooden roof is above the metal roof, creating a 4 inch gap which was filled with blown insulation during the renovation. There are channels which run the full length from the soffit to the peak. When we took the soffit panel off we uncovered 6 channels. The two marked here in red are wet on the metal bottom of the channel. The insulation is not wet at the top of the gap. The other four channels are dry.
Those two channels are also the ones that lead up to the chimney
I suspect that the tuckpointing which has eroded is letting water in and it slowly makes it way down the roof to the soffit.
There is also water in the attic closet