... For what it's worth according to the wording of 300.4(G) a chase nipple cannot be used with conductors #4 or larger since one side does not have an insulating material.
Yeah, I too think it needs reworded. A smoothly rounded surface should be permitted. Smoothly-rounded or flared-entry surfaces [non-insulating] are permitted by the exception, but that's only for integral hubs or bosses... not fittings....
I agree that is what is written, I also think that wording needs changes and have a feeling the intent there is not to prohibit the use of a chase nipple - but I could be wrong. That said I have used chase nipples for conductors #4 or larger many times and have never been called out on this by an inspector. But it is no different then the earlier mentioned driving over the speed limit doesn't mean you will always get a ticket for it.