i think the stock fender looks good. You keep mentioning 1/2 inch lower in the front but that wont make a noticeable difference. the lower you go the less lean angle you will have and those boards will hit the ground real early. i built a new fender just to put my bike back up to stock ride height so i can actually ride it again. being low looks good but a fun riding bike needs some lean angle.

 

I am aware of lean angle and such, but this is a city bike and not something I am canyon carving. I didn't like the "dead space" from the top of fender to the bottom triple tree when the bike was stock, and adding the 21" didn't really do anything to that space. Going to order some different fenders to see how they look visually. But, I know my best and only option is to go the air suspension route.

 

21" looks good. Did you have to do any alterations or change your brake caliper/rotor? Did you lace the 21" to your stock hub?

 

I went from a 16" to a 21" front. The difference in axle height is just 3/4". I added a wrapped fender and lowered the bracket so it sat closer to the tire.