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It is easiest on cylinders that are not excessively rebored, because as standard, there is a considerable chamfer to the bottom edge of the bores that greatly helps getting the rings “started” into the bores. As the cylinders get rebored the chamfer is progressively lost, until by the time you get to +.050 or +.060″, there is nothing left of that helpful chamfer. It’s more of a problem with 600 engines than it is with 500’s as the latter seem to have a bigger chamfer.
It is a job that is MUCH easier if you use a pair of guide rods to make sure that the barrel goes down square on to the crankcase mouth. They are easy to make out of lengths of 3/8″ steel bar. Just cut about half an inch of 26TPI thread on one end, and screw them loosely into the holes that the cylinder holding-down bolts go into. In other words they are like a pair of those bolts with the hexagon heads cut off, but make them a bit longer for ease of use.
I hope that you don’t break any of those precious rings. Use plenty of oil !!