Fast resale on small sports bikes?

Stacee

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My boyfriend wanted to get his motorcycle license but doesn't have a bike to ride. He was going to start small with like a Kawasaki 250 and then move up in a year or two. We have read that it is really easy to sell a 250 once you "outgrow" it. Is there truth to that or should he start out on something like a 650 if hes comfortable on it and not waste the time and effort on trying to sell the 250?
He is 5'9" and weighs about 190.
 
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