I had the same problem using the toe shifter only. Now I tap the heel shifter when in 1st to neutral.

 

The heel tap works best for me, but heck, I can even get away with the 2nd down tap on the toe and hit it most times now. I never had a heel shifter before, and I think it's great, wish I'd have had one years ago; I've got a whole collection of footwear with a fashionable black smudge on the top of the left toe.

 

Funny how these threads keep popping up. Every Harley I've ever owned (and there has been a lot) are difficult hitting neutral. After a couple thousand miles it gets easier, either the gears wear a tad, or you just 'get the feel' of doing it. It is easier if you are rolling just a tad

Good Luck! Oh, and don't ask what oil to use, or what kind of a trike jack do you use