Trying to catch a fish? *nibble nibble*
At 300 low hours I think its pretty clear whats needed.. That's assuming everything is stock. If its already had a few pistons and a bottom end, then perhaps it could be the PV, or pipe mounts, etc.
What you do yourself will depend on your mechanical ability and the time you have to spend working on it.
Quick and nasty test for mains bearings, remove the stator cover, grab the flywheel and see if it has any play up and down. Other than that I'd be looking at pulling the cylinder to visually inspect for damage, and then measuring things up. Generally these 250's like a piston and rings every 100hrs (or less if ridden hard). If the same pistons been in for 300hrs bore is very likely worn as well.
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