You ask why is it failing? Because Harley Davidson Put the cheapest starter clutch they could buy.Some of the car mfgs that used the same clutch as Harley knew of the problems with the standard clutch and switched to the heavy duty .

 

Not related to your overall problem but I would put heim joints on your shifter linkage as they are less likely to fail.

 

Well, I figured it out. After rechecking the wiring I took a closer look at the battery. Though I checked before and the cables seemed tight, in actuality they were not. The poles are somewhat inset meaning they are not flush with the actual body of the battery. So after pulling a little on the positive cable it did come lose because it was not flush against the pole itself. I guess I should have checked that more carefully. I moved the cables to the top since there they are tight against the pole. I took an extensive test ride and shut the bike off at least 10 times. Every time it started right back up without anything abnormal to occur. Lessen learned I guess. Thanks everyone for your input and I hope my negligence will help someone else.

 

check you battery state of charge at rest. charge the battery. disconnect everything. measure the voltage. google for a battery state of charge chart. I think you battery state of charge is below 80%

not a good idea as a regular practice

thats right...the singing is your starter spining up while your engine is...becuase you are holding down the start button. You could burn out your starter.