my starter has started to do the kinda grinding sound, then sounds like it catches and freezes. then if I try it again, it makes a clun,k almost like trying to start an already running bike type of sound .. I'm concerned it could be broken teeth on the flywheel .. which one usually goes first .. and how does a bad fly wheel act or sound? is there anything that identifies a bad starter from bad fly wheel?

I'm not mechanical with Harleys, so forgive wrong terminology. This is my first

Everything is custom, so I can't tell the year or model. I know it's a softtail with an S&S motor

 

Older style you had to pull primary to unbolt jack shaft. New style 06/07 you can pull the starter out the back. Some softails you may or may not need to remove exhaust. Often people replace the starter clutch. Not knowing what you have will make that tougher too. Maybe bring starter to a shop.

Not knowing what you own, makes life tough.

No matter what sounds like you should remove out primary. When you look at end of starter if there is bolt with a washer bent over you have older style.

 

First thing to do is make sure battery is in good shape. Charged, good connections and tested off the bike for it's cold cranking amperage.

All you described will come from a weak battery.

Under load, solenoid magnet drops out, starter bangs, starter grunts, stops.

Do the simple first.