Depends on the gun and the ammo. My 1911's, personally I will only chamber a round a max of 3 or 4 times, 5 is pushing it. At that point, I take that round and throw it into a cardboard box I have with junk rounds that are dinged up, bullets seated too deep, etc and I dont shoot them.
Also depending on the ammo and how hard the round gets slammed into the feed ramp, if the ammo isnt crimped as tight, just chambering it one time can seat the bullet far enough into the case it is visible to the naked eye without a micrometer. So in that case chambering it a dozen times could lead to a major issue if you were to fire that round.
Even when my 1911 goes in the safe, I leave the round in the chamber. Depending how long itll be in there, ride the hammer forward and leave it as is. All I have to do is pull the hammer back, safety on, and ready to go again....
"Better to be judged by twelve, than carried by six..."