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If you do the head gasket it would be easy to do the rings at the same time cause the head will be off and all you have to do then is drop the sump and pop the pistons out the top. Then you put tape around the journals and hone the bores and use a ring compressor to pop the newly ringed pistons back in and bolt back up (minus the protective tape). If you have to do rings later you will have to remove the head and your new head gasket which would suck.
As for the couple of questions you posed the HG does not have to leak oil and water in fact that would be a bad blowout. They actually usually just blow straight through into a water gallery and pressurize the system. And rings can go at anytime. 228k is actually right on the money for rings. I had an engine with absolutely destroyed rings at 100,000 miles and a 20 thou bore lip. Lack of oil changes caused it.
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