Here's a different take on the "upgrade" idea... keep the CBR250R for the street, and get a late model off-road bike, something along the lines of a Honda CRF250X, CRF450X, or an older XR, and learn to ride it proficiently in the off-road environment. Almost anyone with some amount of balance can throw a leg over virtually any street bike and get down the road without too much drama. The roads and streets are full of people (some riding high horse power sport bikes), who prove this every day. Most survive by having good (or dumb) luck on their side. And most will not become what I would consider to be truly proficient motorcyclists.
Learning to ride motorcycles off-road will, in time, put you amongst the very small group of motorcyclists who are truly proficient riders regardless of what bike they ride.
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If I had a teenager, they'd get a 250. Anything bigger, they could buy it themselves. At that age, I'd want novelty of just having a motorcycle period to wear off before they did something stupid got themselves killed.
@Nitrox034232x: To a lot of folks here, they have this 250 on purpose, and have owned "bigger bikes" already. Referring to a change in displacement alone as "upgrading" can come across as a little condescending. Most of the people that have replied are seasoned riders who know what they're talking about.
C'mon, sko sko sko!
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