All learned skills will carry over, I have never been on a 250, as I started out on a 600 and the only bike I had ridden before that was my friends 125 dirtbike in the woods for about 15mins about 12yrs earlier.
I have always been a fast learner with anything on wheels and knew I would not push myself past my limits till I was ready.
All I will say is when you know your ready to upgrade and can push your bike close to its limits when needed, If you feel confident and are willing to not let your ego get the best of you then go for it. Don't let anyone talk you out of what you want just because they didn't do it that way.
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