If you're not Full length sizing and have many loads on the brass, I would consider that the chamber on your revolver is loose and that you're only tightening the neck to hold the bullet in place. The cowboy shooters I know generally don't full length resize because they get more loads out of the brass and they're only getting to above minimum velocity, which saves money on buying more starline brass.
If your dies are in a plate or not adjusted, I can see a scenario where the work hardened brass at the top part of the case has a different appearance than the rest of the case and is in fact smaller, because of the lack of sizing the rest of the case over multiple reloads.
Have you tried sizing with a different die, or see if a full length resize might help? I've used ACP dies when I had my Colt dies loaned out before, without problems.
HTH