Help me find the leak - Updated Pictures

I'd say get in the attic and see if you see a glaring leak and if water is running to this point. However, this may be a tough one because i suspect getting in the attic won't tell you much based on where the drip is located. I would think if it was something above the window in the attic area, you'd see some water spots on the sheetrock above the window.

From the outside picture, it looks like there is water stains right at the seem of the wood on overhang. I'd try to investigate that from the attic as well if you can access this spot.

It may end up coming down to pulling that trim piece off the investigate further but i'd probably do it anyway because if its been occurring often, whatever is behind that may be getting mold growth.

My guess is it’s way up your roof. Roof leaks are very rarely on flat areas, they are generally in a corner, where two inside angles meet, or where something like a vent is. My guess would be it’s running down a beam on the inside and then hitting something perpendicular that then makes it run straight down to your window.

Definitely get it figured out ASAP though as the interior with insulation doesn’t dry well at all and if it’s staying wet that’s a major mold and rot concern.

I had something similar happen in a home I previously sold. There was a rubber seal or gasket around a pipe going out of the roof which was dry rotted and cracked. Allowed a very small amount of moisture to run down the pipe. Tricky part was that the gasket and the "leak spot" were actually about 6 feet apart so that had thrown me off. The angle of the pipe allowed it to travel quite a ways away.