Likelihood of keeping your first brand new bike?

Buy the CB500X brand new, you won't regret it.

I bought a brand new CBR250R last year and planned to keep it for a long time. It did everything from commuting to weekend trips to in Montreal, and it was completely happy on the highways. Well, I picked up my brand new CB500X last Wednesday (admittedly purchased in the doldrums of winter so it was partly a moto fix). Because I have had a well travelled year on a 250 (and a year on a scooter before that) I now know I will have the 500X for a very long time. So lots of money later I would recommend a used bike to start, from a reputable dealer or bought with a knowledgeable person helping you. 3k gets you plenty to start with. Then upgrade with experience and you'll be able to pick the perfect bike for you. Or, jump straight into the 500X--it's a fantastic bike, easy to ride, and great value.
 
New bikes make little sense. The first depreciation hit is 20% off the price, but much higher when people finance. You can find same-year used bike for sale all the time barely used at all.

The typical model pushed by the industry is buy a bigger and bigger bike (at higher and higher margins for them) until you get something with so much power you crash it.

It works like this:

250/300>600sports>750 supersports> crash> Subaru Impreza/BMW 3 series>marriage> kids>Dodge Minivan> Corvette>death

Alternatively..

250/300>600sports>750 supersports> crash> Subaru Impreza/BMW 3 series>marriage> kids> finally get that 1000 now that insurance is cheap> crash

What has changed significantly recently is that they are making small engine bikes in adult dimensions, those old small bikes are teeny.
 
The typical model pushed by the industry is buy a bigger and bigger bike (at higher and higher margins for them) until you get something with so much power you crash it.

It works like this:

250/300>600sports>750 supersports> crash> Subaru Impreza/BMW 3 series>marriage> kids>Dodge Minivan> Corvette>death

Alternatively..

250/300>600sports>750 supersports> crash> Subaru Impreza/BMW 3 series>marriage> kids> finally get that 1000 now that insurance is cheap> crash

Didn't work that way for me. Have you considered taking some rider training?
 
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