Oil temp

Sorry, I said 05 when it is a 95, missed the 9, hit 0.

Your 88in might be different from my 07-96in, but for the first 1K with dipstick temp not digital, my oil ran 235-250, after stage 1 and syn oil on all three on hiway usually 215-220, 220-240 in city traffic...

Yes, for chilly weather if you're talking about conventional. In that case a 20W50 would be better. The 1st number tells you the base weight of the oil & what it acts like cold & the 2nd tells you the upper heat range it can handle. In other words (in theory), with a 20W50 you'd be starting the bike with 20 weight oil, but once it warmed up, it'd be like running 50 weight. And as you've seen, in chilly weather, Harleys never do warm up to the point they do in hot weather, even if you ride all day.

If you choose a synthetic it's different in that they act like a multi-grade & switching weights from cool weather to hot is not necessary. The synthetic I often use (Red Line) carries 2 ratings - SAE 50 & 20W50 but it's not multi-grade. I had a long talk with the chemical engineer & what it boils down to is that the SAE 50 flows so well cold it can pass all the tests for a 20, so it can carry the multi-grade rating & that's what people are used to seeing, so that's what they put on the label.

I use the recommended 75W90 weight gear oil year 'round - used to use the conventional H-D SportTrans then switched to (Red Line) synthetic. Gear oils are rated differently so while that sounds like a heavy oil it's not - actually closer to a 20W50. Problem I have with Amsoil is their advertising, but I know some folks who have used the product for a long time & are very satisfied with it. Really any quality brand is fine - it's the weight & formulation that matters.

And there's one more thing for the primary - the "friction modifier" additive. If you're old enough, you'll remember the days when if you had a vehicle with a "Pos-I-Traction" differential, you had to pour in a little bottle of additive when changing fluid or you wouldn't have "Posi" 'cause the clutches would slip. Nowadays the additive is already mixed in with many gear oils - but not all of them & you have to read the label. But if it says recommended for use in limited slip differentials, you're fine.

Some motorcycle engine oils have the additive too because in numerous bikes (other than Harley), the engine & trans share the same oil & they have a "wet clutch" too. But again, you have to read the label to see if it's got the "limited slip" additive for the clutch. I do not buy the "one size fits all" deal of using the same oil in the engine, trans. & primary in Harley, but if the product has the right formulation you can get away with it.