This x eleventy jillion brazillians. DON'T BUY NEW! Motorcycles depreciate even worse than cars. Craigslist is full of low-mileage older bikes that are hardly ridden.
Well....Maybe not "crashed" but certainly "Dropped." I've been riding since 1982 and I've been in two "crashes", the first one happened in 1990 when I got rear ended at a stoplight by a drunk driver, the second happened when I wasn't watching traffic and locked up my brakes coming to a sudden stop. I wasn't seriously hurt in either one.
I'm also going to disagree with the people here who say a 300cc bike isn't a good starter. If you buy it used and don't wreck it you can probably sell it for just about what you paid. Starter bikes are always in high demand. As for starting on a 600 supersport, just because some have done it doesn't mean it's a good idea (nor is starting on a 900cc cruiser that weighs 500lbs.)
My mantra for starter bikes is: Small, cheap, used. I started on a 450 which IMO is a perfect size to start with.
A smaller (lighter) bike is easier to learn slow-speed maneuvers. Light weight makes it much easier to recover from a sudden change in conditions (like coming to a sudden stop with the handlebars turned.) It's also easier (and less embarrassing) to pick up a small bike after you've dropped it. Watching a NOOB trying to pick a full-dress Harley off the ground is equal parts of painful and funny to watch.Not only are lighter bikes easier to pick up after a drop, they are less likely to break expensive parts when they do.
This is also a good reason to consider a dual sport as your first bike.
People who start on oversized or overpowered bikes often never really 'learn' how to ride well. I see it all the time - people "paddling" their bikes around at low speeds because they don't have the confidence and skill to be able to maneuver at parking lot speeds.
As for those who say you'll get "bored" on a small bike, there's an old saying that goes "It's more fun to ride a slow bike fast than to ride a fast bike slow." I have two bikes, a BMW R1150R and a Triumph Bonneville 790 and I have to honestly say there are times when I think it would be a hoot to have a 200cc or 250cc bike for zipping around town.




Not only are lighter bikes easier to pick up after a drop, they are less likely to break expensive parts when they do.
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(Do you WANT brick-and-mortar stores to go out of business? Because that's how you make brick-and-mortar stores go out of business.) 
