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I'm planning on doing a basic piston swap this winter, nothing as intense as you describe. I am just planning on going to a higher CR, not overbore. But even with just a higher CR there is a lot of stuff that will likely need adjusted to get it to run smoothly.
As far as overbore, i am no expert but from what i have read you will need to get the cylinder sleeved or plated.....or something like that? I feel like if going higher than 250cc is non issue for you, you are way better off getting a 300 ninja then just do some basic performance mods to it.
If you are not overly familiar with 4stroke motorcycle engine and how to work on one and or don't have a decent amount of cash to just throw away paying for other people to do the work and your only reason for doing so is cuz you want a unique streetbike. I just think it is gonna be a PITA!!
I change my mind on my plans about just dropping new piston in and tuning because i think it is gonna be a PITA and has potential to mess up my perfectly fine engine if i get something slightly incorrect. But you are talking about complete heart surgery here with nothing to go on.
Just my 2 cents. Get informed the best you can and try and make a reasonable decision. For the cash you are talking i would be on a 300 in a heartbeat.
good luck, keep us informed, maybe start a blog if you go through with it
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