Ha, no wizard here. I still make mistakes when filing, especially when it's going smooth and I stop paying attention.
But over time, seeing how this chain filed this way cuts vs how that chain filed like that cuts, you can see the differences.
It's like the debate of hook. Different cutting conditions determine the hook. Very little hook but a strong, not thin curve, can cut brush and dirt all day long, maybe with one sharpening needed towards the end. The same chain with a lot of hook would continually pull the teeth into the material deeper/harder, which isn't good when you're cutting brush/sprouts. You're just wasting chain reprofiling the hook and removing any damage.
I had a chain slope back once in my early days when still using the clamp-style filing plates and not understanding. It just rode on the wood, never biting.
I also spend way too much time fixing chains, cause I hate having them ground, as well as having to fix the cutters after having them ground.