Should I

Upgrade cr250 engine to a cr500?

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Upgrade my cr250 to a cr500 engine, still in the 250 chasis?

There is a local dude who specializes in these swaps and he does them for around 500.
I'd say it depends on what kind of riding you do. For a MX track, no. For the dunes, it would kick ass. All depends on what you want out of it.