You are definately in a pre CW site. The ball or "cadet" button is usually associated with Dragoons (early Cavalry), Military schools and the like. However, I have never seen the checkering on one before, so most likely it and your other finds are civilian. Confederates used "flat, coin or penny" buttons throughout the war, and many early CS uniforms (especially TN and KY) sported one piece "flat" buttons. If there are Military relics present, you probably are in a prewar housesite that had CW activity around it. No idea on the brass ring. If it would fit a man's finger, it is probably just that, a ring. The flat spot would have been for engraved initials. Nice finds, David @ Dixie