I know it fits certain older Dyna and Sportster uprights, but does it accommodate a rack as well? I was thinking about using one with this upright and rack combo, but don't know if it'll actually work.

Rack
http://www.harley-davidson.com/gma/g...bmLocale=en_US

Upright
http://www.harley-davidson.com/gma/g...bmLocale=en_US

 

53852-00 rack and 52426-99 upright will fit... Hogrida has one of these on his streetbob with his own custom sissybar so the plug and play should work fine on your bike.

 

I bought one at Delmarva, not exactly what the salesman said it was, have had to buy a different sissy bar, but still working to get everything fitted up.
I have a rack that will fit with the plug n play, I think any of them would. Really no reason any rack would not fit if it just bolts on the rear seat bolt.

 

Yeah, but their webpage doesn't specify...this is all it says:

"Alloy Art's lights have a three year warranty on
the electronics. Alloy Art's led's have a 70º visual
range, the closest light to it in the industry has a
16º visual range, they're also 65% brighter
than standard led's."