Is the case actually clearing the sizing area of the die before it gets hard to remove? Catching on the expander button coming through the neck of the case. Measure a fired case across the neck. Remove the expander rod and expander from die. Then run the case through the die. Measure and compare against other resized case. If the case is being sized to tight could be the problem coming across the expander ball. Check the expander ball for roughness. It could be something with the shell holder fit and alignment. Stuck cases, Caused by insufficient lube, Usually tears the extractor rim off about 270 degrees of the case head not just on each side of the case as you describe. If shells have several loadings they may need the neck annealed the brass is getting hard. Just some ideas to check. Good Luck