Welcome Rockkin to the HDTimeline forum...! Since you have 2 separate holes (1) for the Engine, and (1) for the Primary Chain, Clutch and Tranny the choice is easier.
The Engine being isolated can benefit from cooler running longer life 100% Synthetic 20W-50 Oils not necessarily HD Syn3 which is a blend supplied by CITGO run by Hugo Chavez, who has a very anti-USA bent.
The Primary Chaincase/Tranny/Clutch means Dino-gear oiils without friction modifiers is best in there for long life clutch and high pressure gear meshing with less oil "fling" by the spinning chain.
But read the oil and lube polls and use genuine HD filters, gaskets and such and you won't go wrong...good hunting.