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My advice:
Unless you have a mechanic friend or someone that is very experienced with motorcycles avoid trying to buy used unless its from an authorized dealer. More people than not wreck their bikes and then turn around and sell them. You need to be very astute and know what your looking for when buying a used bike.
As for first bike I'll throw out 2 recommendations:
That Ninja 250/300 is great but a Yamaha R3 is what really catches my eye. Sporty bike that rides more upright and is comfortable. It plenty for street and highway (will easily to 100+).
If you want a little more power without going over the top look at the Yamaha FZ-07. Super great bike that is cheap and offers plenty of power. Its a winner all around.
As for a Ducati Monster, that is a lot of bike and not cheap.
I almost bought a 821 myself, they are sooooooooo damn sexy.
But I read that for commuting they are not that great. They get too hot and the exhaust wraps around underneath the seat and right near your calf.
Lots of complaints about the bike being very hot and uncomfortable unless you are constantly moving.
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