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If you have adequate shop lighting you should be able to see the oil when the bike is upright.
If you can't see the oil then there's not enough.
If you put too much in it will spill out of the derby cover opening.
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Damn son' if your bike didn't have the Leg protection shields I'd say I know you. The guy I ride with most of the time has a bike identical to yours. Exact same setup.
To the OP, add the proper amount of oil to the primary and forget about it until the next oil change. That is unless you have a leak..
My '13 softail manual calls for 32oz wet and 40oz dry. Put the bike upright to fill. I use a 2x4 to get the bike close to level and fill. Before and after both changes I could fit my pinky finger down and just touch the fluid at the bottom of the clutch with jiffy on a 2x4.
Wish Harley would take dry out of the manual. That is like undoing a non virgin...