One less than when it fails.
Seriously, you should inspect your brass each and every time for obvious out of round, split, dented, oversize, undersize, bulging or otherwise mangled. It is really not that difficult to detect something wrong, even on a progressive press. As to how many times you can reload it depends on a whole bunch of things such as the original brass type, the number of loads it has already had, how hot those loads were, the amount of neck resizing done, etc. There is no hard and fast rule. Most people I have read when writing about reloading will reload brass until it is shows some signs of having a problem. Most recommend crushing the casing prior to discarding so that it doesn't inadvertently get used.
How much money I will save when I start reloading. Rifle & Pistol.
It depends on the round and how you load it.
Bottleneck rifle cases that are full-length resized may start to split around the 4th firing if they are not annealed. If you anneal regularly and do not shoot hot loads, I have heard that you may get 20 or more loadings.
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I have had brass make 15 or more trips, before the primer pocket opens up.
When I feel the primer seating is too easy I set that case aside. I will still load it and shoot it but I chuck them afterwards.
Just had some brand new Winchester brass in 7-08 do that, bag of 50 5 or 6 were sloppy loose, one primer fell out after seating the bullet, tried a diff brand of primer loose too. So how many reloads depends on the brass as much as the strength of the load.
Let me rephrase my question:
How much money I will save when I start reloading. Rifle & Pistol.
Give me an example of a 30-06 and 9mm new vs reload
Does your answer include my time spent reloading.
Any input