Remove clutch and clutch basket on 08 flhrc

This is the ring gear on the flywheel that is damaged - they can eventually wear out - however more than likely a faulty starter motor Bendix drive gear or incorrect starting can cause this damage.
You will need to remove the gearbox to replace the ring gear.
There ring gear needs to be heated to expand it for it to be replaced.

Pretty entailed job. Not like a car.
You will need to remove the primary and possibly the clutch basket/ starter ring gear to access an internal fastener holding the starter to the inside of the inner primary.
Will probably need a primary cover gasket and a quart of synthetic (klotz 80-90) primary chain case lube.
While you're in there you should probably check & adjust primary chain tension and the Delrin shoe the chain rides on.
Completely drain the old primary lube, don't mix old with new, the thing only takes 18-22 ozs (so okay, maybe you need 1.3 qts).
Consider the different kW starters available and get the one that best suits your needs (is the motor built? high use? etc...) Terry components makes great components with WARRANTIES!!
Gasket $20-$25, klotz fluid $16-$20.
Starter drive clutch $35 to $100+.
Starter $380- $490 and up
Also jack-shaft assemblies, ring-gears, etc...$50, $80, $$$$$
Finally; if you have a large displacement or built motor you should have compression releases. Use them religiously.

There is no way the ring gear will hit the starter pinion unless the fly wheel bolts on the crank shaft or loose allowing the flywheel to run out of true. If you have had clutch/ rear seal work done lately the fly wheel will only fit in one position and if that was ignored at some time then the fly wheel will run out and touch the starter pinion.. I would also check the adjustment on the starter pinion as it has to be set by the lever pivot to a correct distance or it will touch the teeth of the ring gear

I think this is going to be like an automotive starter.
You will need to check 3 things.
The ring gear where the starter gear cranks the engine, the starter gear that engages the ring gear, and the overrunning clutch or bendix , which is the springy part that kicks the drive gear into the ring gear.
When you remove the starter from the engine, you will see the drive gear on the end of the starter that was inside the motor.
The drive gear is about the diameter of a half dollar or a silver dollar. it should not be chewed up, it should look like a good gear. Inside the place where the starter attaches, you should see a ring gear, with a flashlight, and those teeth should look good and not chewed up.
On the starter you removed, behind the drive gear and usually inside the starter is the bendix or overrunning clutch , which will push the drive gear into the ring gear when you crank the starter. These parts often fail every few years.
Some people fix them, most people replace the whole starter.
Be blessed.

Usually, starter grind is either incorrect pinion gear and clutch ring engagement, or a damaged overrunning clutch drive assembly.

Contact me directly at [email protected] I see that V-Twin does not offer the clutch basket but they do list the starter ring gear. I don't have the parts you need but I may can give you a place to call.

Steve

No, the starter motor is not out of alignment and a shim will not do any good. Keep in mind that I cannot hear what your starter is doing. But, if you say it sounds like it slipping a tooth or a making a grinding noise, it's probably the internal starter clutch. This part is also called an "over running clutch".

This part is replacable but it requires the disassembly of the starter. If you're mechanically inclined and have the time and tools, you can remove and repair your starter and save yourself a few bucks by replacing the clutch. However, if you are going to have to pay someone to do the job, you're better off to have the entire starter replaced. The extra time you would have to pay for to disassemble and reassemble the starter would negate any savings you would have otherwise realized.

Now, there is also the chance that there is damage to the ring gear on the outer clutch basket and the starter jackshaft. I have seen it on occasions. Both the jackshaft and the ring gear are replacable but the clutch assembly must be removed. I would recommend that your replace both if you find either part damaged. Once you find out which it is, repost and I'll tell you how to repair your bike.

Good Luck
Steve

1) Release the pressure on the system by unhooking the clutch handle from the cable
2) Identify which side of the crank holds the clutch mechanism. Probably opposite the chain drive sprocket which means the clutch is on the right side as you sit on the bike. Spray off sand or grit that may fall into the works as the case cover comes off.
3) Drain the gear case oil
4) Remove the kick starter by removing the bolt holding the lever onto the starter shaft. Carefully, maybe with a impact driver screwdriver, loosen and remove the screws holding the round clutch cover from the engine crankcase. There are probably five, maybe seven, Phillips screwheads or maybe with ten mm hex heads. They will be different lengths so remember which holes each came from. I always replace screws with hex head bolts 'cause the screws can be a pain to remove.
5) Remove the clutch cover. You may need to remove the footpeg. there may be a steel ball bearing about 8mm diameter roll out of the center of the basket, so watch for it.
6) The clutch will be covered by a 'basket' held down by probably six bolts recessed into the basket.
7) As you remove the basket, you will find rings made of metal alternating with rings of fiber. Remove these, noting the order. If the metal rings are not blued or scratched, you can use them again. The fiber ones will need to be replaced, at about $7 each. Oil them and put new fiber rings back, starting with fiber and ending with fiber. I smear oil on the fiber plates before I put them in. You will see notches in the teeth at the edge of the fiber plates, and want to not line these up with each other.
8) Put the cover back, usually using a new gasket, or at least silicone. Leaks here make a mess and it's worth taking time to get it sealed.
9) Fill with amount of oil specified on the side of the crankcase. Make sure you use 'cycle oil, with MA rating. Auto oils will allow the clutch to slip, and make it burnout quicker.

This has to be on a Sportster because you can't engage the starter on a big twin with the outer primary off unless you have a special device to allow for it. The torque will destroy the unsupported jackshaft.

On your bike, the ring gear is more or less pressed onto the outer clutch hub. I've seen this before. Now, you can either buy a new outer clutch hub or you can have your old one "repaired". We weld the ring gear to the steel part of the outer clutch basket. But, it must be done in such a manner as to not throw the basket out of balance. Also you must grind the weld down so that it does not hit the engine cases when reinstalled.

Good Luck
Steve

Bad switch or Solenoid. depending on the bike.