Never a stupid question. And great pictures, they were exactly what were needed.
1. Yes they are crimped. The crimp is the slightly larger circular depression around the primer pocket. The purpose is to retain the primer during firing by compressing the side pocket wall inward. When you deprime it leaves the very sharp edge. This makes seating a new primer very difficult because the edge of the primer isn't rounded like the top is.
2. The chatter isn't a big issue.
3. You have not adequately swaged the case. You need to lower the swaging die slightly more. But do it slowly or you can bend the rod. The rod is threaded all the way into the die to where it stops, right? If not your chances of bending the rod are greater. I am including a picture.
Left round was never crimped, but it shows the rounding you are trying to achieve with your swager. The middle round has a crimp just like yours, the right round has a different kind of crimp. I will also include a picture of Federal brass that was crimped and the sharp corner is even more obvious.
