I had a hard time finding it at first on my 95 flstn she likes a light touch when going from 1st to N. It is a really smooth shifting gear box you don't need to stomp to shift.

 

I always go to nuetral when I'm rolling its much easier to find

 

So do I, but it isn't always possible!

My evo has a selector where you can only get neutral from first gear. It will always go straight from second to first. I don't know if this might be his problem?

 

you had me at evo.

 

My brother has an old shovelhead and for years he had the same problem. Turns out that the aftermarket shop manual had the wrong spec for adjusting the primary chain. He was over tightening it. Once he put it to the right spec he finds neutral pretty easily. I'm guessing your friends 98 doesn't have an auto adjust so they may have over tightened it at the last service.