$58 (wholesale cost) for 1000 mile lubes.
I bought my 08 fatbob in Feb with 198 miles from a heavy equipment dealer that is a HD enthusiast and buys bikes from the dealer auction. The shop service manager showed me how to change the oil and filter. It is about as complex as changing the oil in your car. the filter (carquest p/n 84348) comes from the manufacturer that OEM's the harley filter. the difference is that the box says carquest rather than HD.
three places to drain oil from engine,tranny, primary. three different places for the oil - engine 2.5-3 qts, tranny 1 qt, primary 1 qt.
Now that i'm familiar with this bike I will I will be doing the majority of my own maintenance. If I need help there are literally hundreds of shops and independent mechanics that can and will work on your Harley. I don't plan on setting foot in the Harley "lifestyle center" until I'm ready to test ride another one.

 

I think the WIX filter # is 51348, 57348 in chrome.. under $5 most places for the painted, $11 at RockAuto.