For any heat treated boolit, I would normally size as soon as possible and wait at least 5 days before shooting them. I wait 3 weeks for air cooled boolits.
Do you trim your cases all to the same over all length for roll crimping?
Did you change the crimp setting between the .309" and .311" boolits?
Have you made up any dummy rounds and then pulled out a boolit to see if the boolits being shaved or sized down by the case mouth.
Try to fit a boolit sized .311" into the mouth of a case fired from YOUR rifle. If it fits, you're crimping too hard and bulging the case neck.
Are you using a Lyman "M" die or something else like it to expand your case necks and bell out your case mouth?