i might embarrass myself with this response but i had a 1990 Suzuki intruder with the same symptoms . Turns out the shift linkage was whacking into the aftermarket pipes when things expanded when hot. I know apples and oranges but maybe its not an adjustment its something changing with the heat.
i will go away now!
Mazz

 

Thanks. This sucker is bone stock. I haven't touched a thing on it or had any upgrades installed by H-D when purchasing it. The thing desperately needs an exhaust (it sounds like a lawnmower!) but I'm not investing a dime into this thing until it shifts properly.

 

I am thinking; even though the dealer were not able to replicate the shifting problem, there should be some kind of routine adjustment they could do.

Also, are the oil levels correct in the transmission and the primary?

 

Yes sir, I checked all the fluid levels. Eveyrthing is at the appropriate level and clean. I'm really thinking/hoping somethign is going on with the clutch pack (as eveidenced by the scratch marks) and a simple swap-out or rebuild of the clutch will resolve the issue. Harley won't touch it, however, until they can verify a problem. I'll keep you guys updated as to how this plays out. Thanks!

 

Please don't take this wrong,but if the dealer tells HD the lock down adjuster nut has damage they could put improper adjustment on you. Just be ready.

 

Set up an appointment with the dealer to look at it and ride the **** out of it before you take it in...Then demand they ride it now.

 

Mine is opposite to yours. When the engine is just started up and still cold, it is a bit hard to get the second gear in. But once warmed up it works fine. My thought is it is about small tolerances affected by heat, It should be adjustable..

 

Agreed, they could be jerks about it... and I am prepared. I've adjusted these clutches at least 20 times over the past seven years and can happily speak to the dealearship about what happened. The marring to the nut happened while attempting to de-torque it. I wanted to see where the factory clutch was set at so I used an 11/16 box-end wrench on the nut while holding the pushrod with an allen key. This was a foolish idea becaus the factory nut was on their realy good and the box-end slipped. I aborted this attempt and removed the nut properly with an 11/16 socket and never did find out where the factory had the pushrod set. When re-torquing the jamnut I put the bike in gear, have my son sit on the bike and hold the front/rear brakes and I use the 11/16 socket on a torque wrench set to 10 N-m.