So I think I got it fixed. I pulled the starter and inspected the flex plate I couldn't find any spots where the teeth were worn or missing. I did however notice that the shaft bearing on the starter was in worse condition then I thought. So just out of curiosity I put the starter in a vice and hooked up a battery charger to it. When power is applied the starter gear is not fully sliding out and there is a lot of unusual vibration. Went down and bought a new starter, put it in and it fired right up. I drove it around for a while shutting it off then starting it back up. It hasn't done it since.