First and foremost, thank you all for your help. I am glad I joined this forum.

PoolDoc -
After you said "you are leaking water" I went out to the side and sure enough there was water coming out... I have no clue how long this has been going on, because I walk by that area often and have never seen water coming out before. Which brings in a whole new issue. When the pump is running I can see through the window of the backwash pipe that clear water running through it. Keep in mind the backwash valve is down and in the locked position. So why would water be escaping through here.

Waterbear -
My CYA is going down as well, which is probably explained by the above. The autofill is working properly. I replaced it when i moved in and it was turing / off and on as expected.