I still miss them. I suck.
1. Do not upshift early - let the bike pick up speed and rpm for a while and then upshift.
Yes, lugging or shifing too early can cause a shifting problem. Also, ask what oil your dealer set the bike up with. Our manual says Synthetic blend, Scooter Bobs tips say full synthetic.
If regular dinosaur is used, I would imagine run in and shifting would not be great.
Number 1 tip and using full synthetic should help.
If a blend is used, we've used Golden Spectro Blend for years. It helps the most stubborn bike shift easier. It's a friction thing.