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Did you heat the pan up in the oven before you added the corn bread batter? I always preheat the oven to like 450 with the pan already in it with the oil inside and then pour the batter into the already smoking hot pan. That way you get a nice crust on the bottom.
With regard to cast iron, you will know it needs to be re-seasoned if you start seeing rust on it. Otherwise just keep cooking and don't scrub it too hard with soap and it should be fine. If it gets jet black after a while you're doing it right. Also, if you're like me and don't always wash your cast iron pan right after you cook and then it's hard to get clean without soap, heat it up again on the stove before washing it. Once everything in the pan melts and it starts to get hot, put it under some running water and give it a few passes with a scrub brush and the shit will come right off of it. If you're fast, there will be enough heat left in the pan that it will dry itself as well.
With regard to cast iron, you will know it needs to be re-seasoned if you start seeing rust on it. Otherwise just keep cooking and don't scrub it too hard with soap and it should be fine. If it gets jet black after a while you're doing it right. Also, if you're like me and don't always wash your cast iron pan right after you cook and then it's hard to get clean without soap, heat it up again on the stove before washing it. Once everything in the pan melts and it starts to get hot, put it under some running water and give it a few passes with a scrub brush and the shit will come right off of it. If you're fast, there will be enough heat left in the pan that it will dry itself as well.