I could really use some professional advise here. I removed a piece of rotten trim I found while cleaning the gutters. The problem is pretty apparent in the photos with the gutter removed. Water followed the roof at the bottom of the rake and found its way in because there was really nothing...

I am stripping my Trims in the entryway of my house. I removed the paint but then I noticed there is a chippy paint at the bottom of the trim that comes out without any chemical as long as I use a sharp scrapper. Do i have to remove all of this chippy stuff before I stain or can I sand the trim...