The first thing you should do is go get a HD service manual for your year/model bike.
38 fl oz is the correct amount in the primary also the suggestions on the engine oil is correct 3 1/2 qt of oil max in the engine when doing a engine oil and filter change.
Use 75w90 or 75w140 full synthetic gear lube in the transmission Mobil 1 or Valvoline is good products to use, don't use 20w50 engine oil in the transmission even though the HD service manual tell you to.
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08 FLTR candy red sunglo,with 2015 103 HO, V&H Dresser Duals with Monster Rounds, Power Vision tuner, Willy Shiny Wheels and Forks and a bunch of other stuff.