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I learned to ride on a Rebel 250. It was an awesome little bike and really holds its value when you resell. I didn't keep it long though as I never felt safe on the highway. As soon as I got my endorsement, I traded up for a Kawi Vulcan 900, which was also a great bike for me. It was on the edge in terms of reach to the ground, but I had a load of fun riding it. I only kept it for around 10K miles because on longer trips, I needed more power for passing.
My new bike, the Kingpin Low is the perfect height for me (5'4") and gives me all the features I need for a safe riding experience and it gets me on the road, great passing uphill, lots of power to get you out of trouble.
I really hate riding in a group with anyone riding in a smaller cc bike and have pretty much given up on the group riding because of it. We've all had to start somewhere, but I get a little nervous with a newbie on a small bike.
My advice, move up when you can and don't let fear hold you back. Bigger is better and safer in my opinion. Just be ready to practice slow speeds ALOT and then get out there!
 
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