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Go with your comfort. It will change with time and experience. You should push yourself to some extent to learn more, while knowing your personal limitations.
For example, I was flying an airshow with another more experienced pilot, we did not do things that I was uncomfortable with, althought I knew he was able to do them. On the other hand flying home with my instructor we met IFR conditions. I had never flown in true IFR, only under the hood. He has 20,000 hours in 40 years of flying. The experience I gained was invaluable. I will be the first to say that I have alot to learn, and I enjoy learning it.
Tom
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