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Try to take a course if you can, from there it's all about riding with people with higher skills than yours and going places that push your limits. It's rarely about the bike, they all have their strengths/weaknesses.
300's are great because they can really showcase how a bike is supposed to maneuver and perform in turns and corners. Once you master the fundamental skills, the larger bikes will be even more enjoyable because you'll already be aware of their potential and what they are capable of.
More so, once you outgrow your first bike, you'll have a better understanding of what you'll want in your next bike.
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