well I guess whenever I do use the sissy bar bag when going two up, I may just put a towel or something under the bag to protect the fender. I will look for a rack that can be modified to be attached to the sissy bar, or even welded on, then powder coat the whole thing in a flat to match the black denim.

 

All you need is a luggage rack that will come close to fitting the sissy bar and have straight mounts. You know where it bolts to
HD style Dyan models uses a box type mount. Then again it doesn't matter that much a good welder can cut weld and make it look like it was made like that.
I just finished a rack for a guy for a Honda VTX and molded the weld so it looks like it was made that way.
It is easy. If you do not have anyone local I may help you out. It is just a hobby for me.
You can design it and I will do it. I make a lot of custom one off stuff for folks. I will not make anything you can buy that fits. I will alter it to make it fit but nothing that is ready made.
Reduced reach I made for my bike

This is a set of cruise peg mounts I made for a Victory cross country