Tomorrow i will take a new photo of the entire roof to get a good scale for you folks. As i am curious what sort of job i just signed myself up to. Don't get me wrong im not anti-contractor however this is my outlet from my daily geek/computer filled life.
Do you notice something else wrong outside of what i saw with the mold? it surprised me when you mention to redo it all. I'm more of a perfectionist so i dont like that line of shingles not being straight... Maybe theres a better adjective

.. I found another spot which is way worst on the opposite side of the home and it appears that someone has attempted several "fixes".. Will post those while im out there tomorrow.
Thank you for taking time out of your day to contribute.