250cc is a good starting point. That's probably what you're going to be riding in the class. In my experience, most of my friends that started out with a 250 or less, ended up trading/selling their 250cc's after 6 months so they can move up. Most moved up to 600's but a lot of them went to 1000cc's or more. Almost all of them thought they wasted money on their 250's.
There's nothing wrong with starting out in a 250 but if you do, try to buy a cheap used one.
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