Does the bike roll when the clutch is pulled and the tranny is in gear?

That would isolate the issue down to either the transmission or the engine, but I'm guessing it's the motor. I think jarhead is barking up the right tree on this one.

 

Pulley bolts?

 

I was WFO on my Kawi triple over 100 and it seized, I grabbed the clutch and coasted over a mile getting of the I-10 bridge. I rarely take my hands off the bars after that day.

 

Yeah, your most likely culprits are Pulley/Rotor bolts backing out and catching the swingarm, rear brake seized (is the rotor discolored?) or the oil pump failed and the motor seized. Just because there is oil doesn't mean it's getting pumped.

 

Don't think it's pulley or rotor bolts.

 

Not necessarily. He didn't say he spun the wheel 360*, only that it spins freely. Back and forth a few inches on the ground or even on a lift doesn't prove anything definitively.

 

wheel bearings, sprocket bolts, rotor bolts those would be my guess one of them

 

In order to get the motor spinning while pushing the bike, you may need to put it into 5th or 6th and perhaps loosen the spark plugs, other wise the compression (if you have any) will keep the motor from spinning easily. I don't think this was mentioned, but I once had a miss-fire break off a valve which quickly wedged itself between the piston and cylinder, not good for the motor but it added some excitement to the ride....

 

the starter just clicks, and it rolls freely.....

sounds like engine to me, but who knows.

My faith is being rocked in these harleys.

 

Glyd, don't let your faith go. We're talking about a 10 year old bike, first year of the Twin Cam. And we don't know the maintenance record. Early Twin Cams did have problems with premature cam chain tensioner wear which could lead to oil pump failure among much worse things.

All mechanical devices will fail and/or need repair. Harleys of today are just as reliable and face the same problems as any other vehicle on the road.