I'm sorry for the confusion. The house was built in 1965. I'm not sure how old the roof is, but I would guess it was done within the last 15 years. There are two roofs on the plywood. I'm located in New York.
As you mentioned, the plywood is cut about an inch and a 1/2 shy of the fascia. I have aluminum gutters with downspouts in various locations. I will take some pictures tomorrow to illustrate this. I took a video of the soffit leaking, I'm not sure if that helps: http://www.youtube.com/watch?v=eFHmxDuTWJM
- Not sure if there is a way of attaching video.
I was thinking that the gap between the plywood and fascia was the problem and that's where the water getting into the soffit. I was considering putting flashing to close that gap? No idea if that's the right thing to do.