My fender was pointed up with the bike lowered an inch. It was just something I noticed a lot. Look in to some fender lower kits but there's not much out there for the 14s yet.
By leaving the rear bolts in place and pivot the fender down and re drilling the front bolt holes the fender is level and still has 5/8" clearance. I think it looks better and the cheapest mod yet. Just putting out there..

 

That looks good. We have the same bike so it's neat seeing the mods you've done.

Was the nut on the inside of the fender welded? Easy to move to the new hole?

 

Look at this thread from Touring models it should answer your questions if not hit me back. Post your favorite pic of your bike I'd like to see it.

https://www.hdforums.com/forum/touring-models/1041671-lower-the-front-fender.html