also make sure you take your foot completely off the shifter between each shift..

 

One more question for the night. Does the bike have the standard foot shifter and floor boards or does it have forward controls? I have heard of forward controls binding and causing shifting problems..

 

Standard boards (replaced today with some take-offs from my ultra) and standard shifter set-up.
Only thing I need to verify is the shift linkage has a 45* near the transmission lever to clear the true dual for the rear cylinder. I need to double-check if that is Harley design and if it allows proper travel. Surely it couldn't have been on for all these years and not functioned properly - but after seeing a couple of other things on this bike, I'll research it.
Side note nothing to do with the problem. I was going to eliminate the crashbar (nasty and flaking) going for an Old Skool look, but found out after removing it that the plate that supports the right side floorboard-master cylinder-and brake pedal, only has 1 3/8" bolt attaching it to the frame - so the crashbar is the second point of support structure. Bad design. Don't want to weld it to the frame, so new crashbar ordered.
Attached a Pic of my sons FLSTC.

Here's the one I'm working on.

 

You should check your primary chain, it may need to be adjusted.

 

I would get it up on a stand and see if the clutch is actually disengaging fully.

 

Agree that clutch adjustment and primary chain adjustment could be the cause.

Also take a look at the shift lever at the transmission, make sure it is tight on the shaft, no wobble at all.

It these items don`t fix it, check the shifter pawl adjustment, the process is in the service manual (very easy).

 

Well since you said its good 5-4 and if the shift arm at the tranny is oriented right and not hitting anything I'm kind of leaning toward bent or distorted shift forks, but I hope not. What Dan mentioned would be easier to do before you go after the forks..

The other option is once you get into 5th, just don't ever stop..

 

Thanks everyone. Clutch is completely disengaging. Next weekend I'll check it all before the new primary and fluids.
Too pretty today - going to get on my Ultra and find some winding backroads.

 

Yup, just got back from a 150 mile run in the country..

 

I still haven't gotten to it, but this weekend I'll attack it. My son (HD parts guy) ran my VIN and found out there was a recall, repair, and the warranty adjustment made to the shift pawl on this bike. Any thoughts on a BAKER anti overshify pawl and it's quality?????

Tossed old crusty primary - Inspected clutch (all Good - check) - adjusted clutch (check) - adjusted primary chain 1/8" (Check) - installed new primary & Derby cover (check) - filled primary with Royal Purple Max (check) - adjusted shifter pawl 1/8 turn (check) - replaced shifter shaft bearings/bushings (check) - put everything back together.
Shift up and down, smoothly and neutral is easier than before.
Not sure which step did the most (I'll say pawl, then primary) but she's good to go now.
Tomorrow Trans fluid to Royal Purple - a slightly softer clunk would be nice.
Thanks everyone for your input.