So I have had some primary leaks and taken the whole dang thing apart down to the front pulley on the transmission (which includes the pipes, oil tank, and starter on a '95 softail...cripes!). So now I'm looking at the drive belt and a curious thing happens...when rotating the wheel forwards the belt pulls to the outside or left side of the front pulley and starts to audibly rub (I can hear it making a squeaky shoe sound) and clearly it is tight against the outer rim of the front pulley. The belt returns towards center of the front pulley if I rotate the tire in reverse. WTF? Is something not aligned? Warped? Or is there some law of physics based on being located in the northern hemisphere that naturally causes that? Now I'll admit...a while back I put on a fat boy replacement tire because I got it for $20, and because I'm a cheap bastard I bought a $20 spacer and pushed the rear pulley out so the belt wouldn't rub on the tire instead of spending another $100 and just getting the right size tire!!

 

That is normal for the belt to run out going forward, in going reverse.
I would check your alignment and tension if it is rubbing enough to make a noise, and it should run all the way in in reverse not just half way.

 

sorry dup

 

So you spaced out the rear pulley but not the front? I'd say that is your problem.