I never shift into neutral except for when I am warming up the engine for the first time of the day. It stays in first at stoplights and when parked. But I have never had a shifting problem with any of my four Rebels. Rebels are often used as beginner bikes, and beginners can be awfully hard on transmissions, probably moreso than any other part of the bike. I have had new bikes that simply did not shift that well. Usually a slight blip of the throttle works wonders. It helps the gear dogs mesh.
2016 Rebel, 2013 Royal Enfield B5, 2009 Genuine Stella, 2006 H-D Sportster 1200, 2006 Vespa GT200, 2001 Yamaha XT225
"I refuse to believe in a risk free society where the thrill of living is traded for the safety of existence." — Nick Ienatsch