Not sure why they even waste $$ putting that fitting there. I've disassembled numerous Harleys to the bare frame and have NEVER seen a steering neck bearing problem, not one. None of the necks were loaded with grease which is what happens when you pump grease into that fitting. Unless you drove your bike under water I see no need to grease that fitting, the bearings are packed at the factory before they are installed and should remain happily lubricated for the life of the bike.
Below is a picture of your neck bearing's. They do pack them at the factory but ask you to have them serviced at the 1K service for a reason. They are cup and cone bearings like used on trailer wheels. Not sealed! They do take some pounding from bumps and whatever. The reason you are supposed to fill the chamber with grease, as you turn your forks back and forth, the grease that is packed from the factory is eventually pushed out, leaving the bearing not properly lubed. Filling the chamber will keep grease in the bearing. Sorta like buddy bearings on a boat trailer, but not that much pressure! It's also a good idea to use a ggod High temp grease that won't turn to liquid and run out in hot weather. Check the bearings for proper adjustment too. I keep mine a little on the tight side. 1 1/2 swings! Never had front end wobble.
Everyone's got their own opinion and while I haven't seen every single H-D steering neck bearing that was ever disassembled I have seen more than most. I have never seen a dry bearing and, ironically, the last set of triple trees I had disassembled were off of a 79 XL (that's a THIRTY THREE year old bike) with over 50K on it. There was no excess grease in the neck and the bearings were fine, so good in fact that all they got was a bath in the parts washer, dried, inspected, repacked (old school, by hand) and reinstalled.
My $$ say's they'll go another 33 years with nary an issue.
Why not just pump it a few times and leave it at that? Whatever amount that is in there will spread and cover everything, Why does it need to be packed? It is not like you are packing the bearings them selves.
I always greased mine goose neck bearings, but still went bad at 65K made me feel very unsafe in sharp fast turns.Shop was hesitate to replace em under warranty but after few nice words from my mouth I was able to convince them and that was 4 Hrs job plus parts.