For the sissy bar, just shorten it from the bottom so fender fits the tire shapes.
One thing I noticed is your fuel tank. It looks like you have the bungs in the stock sportster location. With the angle it's mounted, you are going to have about 70 mile range of fuel. I know this because mine is the same way. I lose almost half of the tank's usable volume both below the petcock and above the fill neck. I just live with it as my chop is a survivor and I'm not fucking up the original custom paint to move the petcock to the lowest point, or the fill neck to the highest point.
Not tryin to bum you out, just passing on my experience with frisco'd tanks and stock location fittings. The paint looks killer, I'd leave it and ride, at least until the next paintjob comes around, or you find another tank to modify.
Kickass Chopper regardless. Wiring is simple, the trick is to keep the harness clean and simple. The diagram Travis posted is right on!!