It's been a long time since I delved as deeply into the construction as you describe. But I would concentrate on the drain pan. All of the water that drips off any part of the air conditioner should drip into the drain pan. In earlier days (including 2007) the drain pan had an opening that simply drooled the water onto the roof, and it ran away in whatever direction it could. Sometimes an unexpected direction, especially of the crown of the roof was collapsing. More recently, a clear vinyl hose was attached to the drain pan outlet, and led a couple inches over the edge of the roof. Now the water drips onto the ground.
You might try adding a nipple to the drain pan outlet if it doesn't have one, and then adding a length of vinyl hose over the edge of the roof.
Of course it goes without saying (but I'll say it anyway) that the nipple and hose must be cleared of all gunk and goop that might block it. Again in the older days, it was common to find that the drain pan outlet was clogged, making the pan overflow in areas where it wasn't supposed to.
Let us know.
Bill
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