Things went better this evening, I hunted the stand I saw a bunch of does under after dark. This buck came out about 100 yards away and fed my way at the edge of the pasture. I heard more deer across the field in the woods and this buck walked up the hill in front of me to check them out. He had been in line with my neighbors house until he headed up the hill. I shot him at about 60 yards, I hit high in the shoulders, broke both of them but apparently didn't hit anything vital. I got down, reloaded and walked to where I could corner him in a ditch and finished him off with a neck shot. My deer drag-a-matic pulled him out a deep hollow easily, about a 150 foot pull.
The gun is a TC Hawkens kit gun I built this year, my dad had the kit for over 35 years but never worked on it. I wanted to kill a deer with it because of the family history the gun had. I finished the rifle and showed him pictures of it finished when he was 100 years old shortly before he died.