Relatively new to Harley. Had (and still have) Hondas for 30+ years. When I got the bike last fall with about 9000 miles, I immediately changed engine oil (Mobil 1 20W50), and primary oil (Harley Formula +).
The shifting seemed a little rough, that is, a little bit of grind between gears. Checked primary chain. It was a little tight, so I adjusted. Also properly adjusted clutch play. Shifting somewhat better, but still not smooth...unless I shift slowly. Then no grind at all.
Is there something else I should check? Re-adjust primary chain? Use different primary oil? Continue to shift slower?
Bike stored for winter now, so lots of time to consider options.
No matter what you do, the Harley will never shift as smoothly as the Honda. Transmission gears are much larger, they have a lot more inertia when shifting. With all adjusted correctly, you'll still get a clunk when shifting. Just the way of the beast.
There's one thing you can check that causes Sportster shifting problems.
The shift shaft, the part the shift lever is bolted to, should have some in/out end play. If not the inner shaft bushing has walked out of the inner case.
The remedy is to hit the end of the shaft with a dead blow hammer until there is end play. That will re-seat the bushing in the case.