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My friend who has a 2017 Indian Roadmaster used the 20w-50 Classic and it has been running great. 5k miles and no issues. He'll change it soon and said he would use it again.
Overall VR1 is probably a better oil, made with a modern SP additive pack with boosted ZDDP and more ZDDP than the Castrol, also the Valvoline is mostly Group II while the Castrol is mostly Group I, I haven't seen a full VOA of the Castrol but from the datasheet I know it has less ZDDP than VR1, and VR1 has a good VOA video here, I don't know if the Castrol has any friction modifiers but the VR1 does, I can tell that at least the Castrol probably has SN levels of calcium and not as much as some older formulation A3/B4 oils and CI-4+ diesel oils since it's .95% ash but I don't know if it primarily uses calcium detergents or if it uses a calcium/magnesium blend like modern SN+ or later lubes.