I know this is going to start a crap fight, it always does...
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First, know how to anneal correctly.
Just smearing the case neck with temp color change paint and laying a torch flame to it is NOT correctly annealing.
Its quite difficult to anneal thin brass correctly,
And if the brass changes color right away, you have overheated it.
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Now, as to how often, depends entirely on your application.
Common range/practice/plinking ammo, I have to go with every 3 or 4 loadings.
'Match' or bench rifle ammo, each & every loading.
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As to 'Cause', the chamber determines the lifespan of the brass,
Loose, sloppy chambers will allow the brass to expand a great deal,
Resizing further work hardens the brass,
So it needs annealed more often.
A good, tight chamber, or only neck resizing if the brass is going back in the very same rifle will extend the life of the brass and reduce the need for annealing.
You don't get that option if you are loading for more than one firearm in the same caliber, in that case you have to full length resize everytime,
And that increases work hardening...
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If you use flame, SMALL TORCHES!
Take a little TIME, to get to proper temp so the case heats more throughly, instead of super heating the outside before the inside reaches proper temp.
Everytime I see someone using a plumbers propane torch I cringe!
The little butane torch heads do a MUCH better job...
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Rotate cases, AND/OR use multiple flames from different directions.
Electrical induction annealing solves the inside/outside temp difference issues, but is more expensive.
Use the color change temp indicating paint on the INSIDE of the cases!
Painting the outside, then hitting it with a torch tells you nothing about what the case was doing.
When you paint the inside, angle your torches up a little, not blowing down into the case/paint for an accurate reading... (Another really common mistake)
Personally, I don't worry about the brass changing color,
I use a pyrometer instead of color change paint,
Its a one time $20 purchase that doesn't dry up between uses, and its more accurate anyway...