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If you already know the basics of riding and you respect the bike you could probably start on something bigger with out a problem. With cruisers you won't have as much of a problem with bigger engines as you would with sport bikes.
The 750 Nighthawk isn't a bad bike and you can usually find them around, and both Honda and Yamaha make nice bikes with bigger engines as well.
If you go the Harley route, know that you will end up paying a lot of extra money just for the name.
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My life is one of those 'you had to be there' jokes.
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