Is the target backer vertical or at an angle? If it's vertical, they do look like they're keyholing to me. How's the bore look? Rifling consistent the full length? One member had a 204 Ruger Handi that was only rifled in part of the bore!!
Tim
38gr H380 is a start load, max for a 50gr Sierra is 41gr, and if you're loading to the lands, you're loading longer than normal COL which will reduce pressure. Try more powder in .5gr increments to the max of 41gr and see how it goes. Same for the H4895, 33.5gr start, max of 36.5gr.