Clutch problems
Shot of that on the trans, the trans cover needs to come off to check the shifter drum and shift legs rods, and if you still don't find the problem, then trans need to come apart to find the problem, such as rounded dog legs on the gears that is causing the clutch to pop out of gear (if you did get the trans all the way in 6th gear).
As for clutch, would power bleed it to get new fluid in the system to start with so your getting a full throw on full lever, then adjust the clutch adjuster on the basket correctly as well, if the hard shift problems is the clutch itself the problem. Hell, at 9k and hard clutch usage, may have a spring plate rivet that broke loose, and is stuck in the basket/plates to cause the clutch to not fully disengage in the first place. If after market clutch, such as extra plate that replaces the HD spring plate, may not have been installed correctly, causing it to not fully release on lever pull.













