Reloaded ammo changing over time mystery

Maybe focus on what your cases are running into now - paint up a case with Jiffy Marker - where the case hits whatever, the Jiffy Marker will be rubbed off - can investigate what if anything is exactly there, or what, exactly, is on your case. Focus on the "what is happening" - not clear that you know other than "it will not chamber". Once you know the "what" - can likely fix it, and that might give you part of the "why" that changed?
 
If it were me, I'd be looking in the following order:

First: dirty chamber (these headspace off the rim, so look there for some wax/lube/dirt/etc buildup.

Second: The old roll-crimp bulge - easy to determine with calipers - just run them through a lee factory crimp die and you're good to go. If I was a betting man, I'd put my money on this one.

Third: carbon buildup in the throat area just ahead of the chamber. You don't need a bore scope for this (but it's easier if you have one). Just a good cleaner like carb-out. soak the area and let it sit. A little scrub and patch it out. repeat a couple times and see if the problem goes away.

Fourth: Lead ring buildup in chamber / throat area - if you shoot a lot of cast, this is a possible culprit, but the hardest to deal with.
 
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