the oil is pumped through the filter, the routed through passages in the case to the end of the crankshaft, where the seal is, and up to the lifters and valves. hte most important one is the one that goes to the end of the crankshaft. That one feeds the main bearings, rod bearings and oils the cylinder walls and crankpin with the oil, by splash, as it comes out of the bearings. If that seal is damaged it could stop some or all of the oil from going into the crankshaft. this can lead to great difficulties.
The top end oil goes through another passage is in unaffected by the seal.
I'm not really sure what you mean about the oil going into the crankcase. Oil should go into the crankcase, but it also should be pumped out by the scavenge side of the pump. What symptoms are you getting that oil is going the wrong place? Does the engine have any clunking noises? Questions for a nosy mind and a source of data to figure out what is really going on here.
As for the Super Meteor and Trailblazer, they are the same bike less some minor appearance changes, like handlebars, the casquette headlight was on the 54 or 55 and later Brit models, not the Indians, the mufflers may have varied a bit.
Very minor stuff. The numbering was probably the same. It was a cheap conversion.