If you look at about 0.41 seconds on this video you get a good close up view of 3 to 4 inches of the teeth on my buddy's clutch sprocket
that are just wiped out and will no longer engage with the starter. The bike is a 2006 Sportster 1200 XL with maybe 60,000 miles on it.
What do you think would cause that to happen? Thanks for taking a look at it.

 

My guess is that the starter solenoid got stuck at some point, which means the starter shaft didn't retract.

 

Started spun before full engagement

 

Did he hit the starter button with the motor already running? Not sure it that would do it or not.

John

 

IDK. Foot on the brake + bike in gear + clutch out + hit the starter. That ring gear on the clutch is pretty stout. Whatever it was must have sounded pretty bad when it happened.

 

This is like asking how many licks it takes to get to the center of a Tootsie Roll tootsie pop. It can be as stupid as a loose starter.

 

I'm pretty sure it's 25 licks. I'm sure others will correct me.

 

Yeah I won't even attempt to figure other humans out..... mechanical $hit I can fix.

 

God has a defect bin in the end because he couldn't even fix them

 

OCSpringer>>IDK. Foot on the brake + bike in gear + clutch out + hit the starter. That ring gear on the clutch is pretty stout. Whatever it was must have sounded pretty bad when it happened.

I have noticed that he will often start his bike while the transmission is in gear, just pull in the clutch lever and hit the start button. While personally I never do that,
I just take the time to find neutral and then hit the start button. The starter just doesn't need the additional drag of turning the transmission along with the engine when starting.
I was taught/told that you will put less load on the starter that way and it will last longer and just be easier on the whole starting system. Which is beginning to make complete sense
as far as his problem goes. I told him this theory of how and why to start a bike that way but he never really took to it and I didn't really insist. And by the way this is his first motorcycle.

So I think I may have answered my own question here. Most always starting the bike in gear could substantially add to starter load and cause something like this to happen.
Thanks for all your input as it has helped point out a number of things to me. p.s. and this is something he knows at some level, he is not a great mechanic but he is learning the hard way.