how to know when to bore cylinders

You have to measure out the bore. You should get close to 75mm. According to what I read if your at 75.02 you should go for a bore up to 75.25 mikesxs sells the pistons and rings. How marked up are your pistons on the thrust side? What do the cylinder walls look like?
 
Your cylinder and pistons are marked with the original factory sizes they came as. Compare them to what they are now and that will give you a pretty good idea if they're serviceable or not.
 
Re. measurement of cylinders, it's not that simple. If the top of the jug is lipped from wear it has to be bored. If the cylinder is pitted it has to be bored. If the bores are in good shape it's possible they can be honed. Let a machine shop evaluate and measure the bores for you. You may be able to use your current pistons and maybe not.

If boring is required the shop will be able to tell you how much material they'd have to remove to get the bores clean, and based on that you'd select the appropriate oversize, obtain the pistons, bring the pistons to the shop, and then have the cylinders bored to them. Piston oversizes are specified in increments of .025 mm.=.010". If they tell you, for example, "We'll need to go twenty over," that means you'll need a piston .020" larger than what's in place--2nd oversize, if your current pistons are original.
 
Most places will measure for free or very close to it if they think you will have them do the work. I had the local speed shop do mine. Second overs, $35 per hole.
I would have gone just first over, but found a set of new old stock second overs for half the price of new first overs.
Shop around you might find a deal on the pistons.
 
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