If you're seeing it with increasing charge I would say it's most likely pressure related and I would back down. I have had loads that just wanted to shoot really warm and left a slight imprint on the case head. No other signs of pressure just like you're saying. As a young reloader wanting to confirm, in that particular rifle I went up in .2 grain increments and IIRC somewhere around 1 gr further started shaving brass off the case head, then soon after locked up the bolt. Had I known better, I would have stopped at the really shiny ejector mark indicating definite brass flow into the ejector, instead of pushing it to the point of heavy bolt lift.
It's going to come down to a comfort level and brass life. Those loads that were leaving a "slight" imprint were definitely warm and brass did not last very long. I'd say 7-10 rounds before primers were too loose to hold a primer. I say comfort level, because i have no idea how high that pressure is without equipment, and how close that particular load is to the point of locking up the bolt. You probably know this already but every rifle is different and Some powders are more sensitive to changes in temperature and can cause an increase in pressure sooner than others. My personal absolute is a heavy bolt lift. If I feel a heavy bolt lift I am on the brink of stupid. How long are your primer pockets staying tight? If you're losing them at 5 reloads I'd say it's definitely too hot and waste of brass.
Since i've "grown up" in my reloading, during my initial ladder tests/pressure testing i stop when I see an ejector imprint or slightly heavy bolt lift which ever occurs first. I call that my pressure limit and stay clear of it by at least .5gr if not more depending on the cartridge. I've also started using quick load which helps but I also take the pressure ratings with a grain of salt.