We are repairing and painting all of the wooden trim on our (new-to-us) 1930's home. We have a brick chimney on the gable end of the house, approximately 6 feet down from the ridge. The roof is a double-roof (ugh): there's a layer of asphalt shingles (in good condition) laid down on a raised platform over the original roof. Water appears to be dripping down from the flashing (visible in the photo) around the chimney and onto the crown-molding and fascia board (correct term?). I've removed the rotted wood from the end of the fascia board in the photo, and I was going to repair that damaged end with Minwax Wood Hardener and then Minwax Wood Filler.
The crown molding piece appears to be solid, but it needs to be reattached more securely which will reduce the width of the gap between the molding and the fascia board. I will then caulk along the underside of the molding to seal that gap between the molding and fascia board.
But what should I do along the brickwork/wood interface to protect the ends of these boards from further water damage? Extend the chimney flashing out and/or down somehow to the vinyl siding? Install a drip edge on top of the crown molding (essentially, between the two roof layers) for the six feet of roof between the chimney and the ridge? Do I also need to further protect/caulk where the vinyl siding meets the chimney for the rest of the way down to the ground (probably not, I think)?
Thanks for your suggestions!