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You might want to check your HD warranty. Belts and pulleys are considered "consumables," meaning they aren't covered. The reason I mention that is that if additional damage occurs due to belt failure, it won't be covered either. I guy I sold a Night Train found that out on the way to Laconia. Cost him a grand out of pocket to get everything back together. An ounce of prevention...blah blah blah.
 

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My $.02 worth: chains and sprockets do a great job IF you maintain them and replace them when needed. If you don't, a chain failure can be anything from simply peeling off the sprocket onto the road, to violently wadding up into the drive sprocket, locking up the rear tire, smashing inner primaries or similar parts, etc. I watched my pal take a vicious crash on his Ironhead Sporty when the chain failed as he was leaning into the I-95 on-ramp. High sided him right off the embankment. Was it his fault? Probably. It's like the FAA crash analysis reports; they virtually always blame the pilot if the engine fails for not noticing a potential flaw before leaving.

Belts are great for the "cruiser" crowd because they require virtually no maintenace or even adjustment. Shafts are even better from that perspective, but they obviously have their trade-offs in weight, handling, and power loss.

When I got the LR it had this neat oiler that dribbled motor oil onto the chain as the bike went down the road. Said oil would then fling up into the air and all over the back of the bike, underside of the fender, and the passanger's shirt/blouse/jacket. Them was the days!
 
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