Well, I am always one to try new engine and tranny oils...
1) Engine, after I got my bike 2 1/2 years ago, used MA JASO rated Dino Oils, as was customary with motorcycles having 1 hole for engine, primary and tranny. HDTimeline visit convinced me the error of my ways now knowing there were 2 separate, 1 for engine and 1 for primary/clutch/tranny. Since Mobil I V-Twin was not available locally and was very expensive $10.99/Qt at the time.
Engine: I used Lucas 100% Synthetic 20W-50 Racing oil for $6.99/qt that is approved for use for motorcycles and Harley V-twins...for 3 years, no problems. Oil comes out pretty clean (but I do change it often every 3000 miles, and goes in pale gold, used comes out brown amber in color. Recently O-Reilly's Auto Parts had Mobil I 100% Synthetic 15W-50 on sale for $4.99/qt and so the jury is still out as I just changed to it only last month.
Before I get a whole lot of flack here for going this route, let me explain...I am going along the premise that SoCal has very mild climate changes and my 2004 Sporty is my daily driver. I have never had heat control issues, after completing my stage I mods. Quite the contrary, because I have only 4 mile ride to work every business day, I do not get my oils up to full operating temperature except on weekends (though I have been in the Central Valley quite often, at greater than 110 deg F), so I do change my oil more often then what some would consider normal. Oil changes at 1/2 price is a significant savings.
Tranny/Primary/Clutch: Spectrol Gold 85W works great, nice and quiet Dino/Mineral based gear oil it is compatible with oil wetted clutches, runs nice and quiet, goes in pale gold, drains out gold, with very little deposits on magnet. Could not be happier.