Some things to consider:
1. If you have a SAAMI chamber, and are using regular FL sizing dies with an expander ball, you are working the brass big time. You can be expanding the neck 5 thou or more on firing. Then risizing it down by 10 thou or more, and then expanding it back up again with the expander ball. For sure that work hardens the brass fairly quickly. Despite that abuse I have had .264 WM Winchester cases last up to 20 reloads without cracking. If nothing else it shows how much abuse the brass can take.
2. On the other hand if you have a tight neck, turned neck OD, and use a bushing die without an expander ball, this whole cycle of expansion and contraction is reduced by a huge amount. The issue then becomes more one of uniform tension than preventing cracking.
3. If your last sizing step is a reduction with say a bushing, then as your brass work hardens, you get more springback, and tension is reduced. If your last sizing step is an expansion with an expander ball, the reverse happens. More springback gives you more tension. I use a hybrid method and use a bushing which minimally reduces the neck size, and then follow that with an expander ball that just slightly increases the neck ID. I feel that method is less sensitive to brass work hardening effects. I have gone 5 firings, and not noted any significant difference in feel, or required a bushing size change. But, then I just go by feel and have no fancy seating pressure measurement system.
4. And last the amount of softening that the annealing process does is highly dependent on the initial hardness of the case. See the graph below which illustrates how much the hardness is reduced with the same annealing temperature and time, but with three different hardness states. The harder it is (yellow line), the more effect annealing has. So if consistency is your objective, letting the brass get hard will result in a big change. And on the other hand if it is soft already (blue line), you may be essentially doing next to nothing or nothing at normal annealing temperatures. And just a personal theory, but I suspect many are annealing at too low a temperature to do much at all. By my estimations you need to reach about 875 deg F for 7 seconds to anneal harder brass. At 750 to 800 F for a few seconds nothing will happen.