there's definitely drip edge and it juts out enough so that the water runs directly into the gutter. I think you're right about not enough ice shield due to the buckled shingles. I think the water was pooling in the soffit. When I took a level to the pine soffit pieces, some of them slope towards the house just enough so that water would eventually drip down the siding. No evidence of wall wetness or damage inside. We also have 1/2" foam board behind the siding so I believe the water is leaking between this foam surface and the backside of siding, but hopefully not on the backside of foam and OSB. I need to a roofer to take a look.