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HD's crap oil was only in my bike until I ran Mototune new-engine break-in...then swapped to M1 20w/50 v-twin synth & swap it every 5K (w/filter, of course).
No need to do every 5k for primary and tranny unless you have to much money or to much time. Or you enjoy overkilling.
10k for primary, 20k for tranny.
ninetyzero, I change all three holes at 2,500 miles for the same reason you lock your house doors. It is good for you mental health but doesn't really make you any safer.