Tim has the best advice, new steel flywheels is many many times safer than old flywheels. However, running with two RH flywheels that already has the oil channel drilled would not meet any particular problems at all. I don't know if you really mean running with two Left Hand flywheels that does not have the oil channel drilled? Well it is possible to run two LH wheels but not really recommended. The reason for the oil channel is to provide a better lubrication to the rod bearing. How much oil that is transported via that channel is a matter of debate, but the air opening and pulsating crankcase pressure makes it easier for the oil mist to find a way in to the bearing. It might be the case that you have found an earlier crankshaft in your engine! All earlier Indian engines (except the ACE) did not have any flywheel drilling and thus had simple splash lubrication for the rod bearing, but the oil distribution and ventilation was a bit different in those engines. Oil was dripped directly in to the crankcase compartment and air and oil mist flowing into the cam compartment. On the 101 the oil is dripping into the cam compartment and the mist of air/oil is directed in to the crankcase. I am almost certain that for fair weather and light use the oiling would be sufficient with a undrilled RH flywheel, but with care and a bit of presicion, drilling that cannel is no real problem to do for a reasonable experienced machinist. But New steel is way safer. A broken flywheel can put a serious dent in both your wallet and your nose.
