Motorcycle transmission 2004 883 sportster, my gears... all of a sudden became hard to change gears...seems to be some "play" when moving the gear lever...notice a little oil on outside of bike in that area....doesn't seem to be the clutch....i can change gears but only by moving lever up and down until it gets into gear....harder to get to higher gears....

Transmission may now be toast since you continued to drive it when maybe low on fluid or torque converter had failed. How long since last fluid and filter change? Ever?

automatics do not change gears
the gears are constant mesh and the ratio changes ( gears) is achieved by bands and clutches
change the transmission oil , and have the bands and clutches adjusted

Possible wear and tear on the gear linkages/ the shaft/ the gears or the failure to notch.
All this relates to a possible fault within the gear box , check for PLAY of the gear levers/linkages, if worn out change them so that the links MOVE perfectly when the lever is moved to change the gears. Also check the gear box OIL within , if the oil seems to contain metal particles then you need to open the gear box without delay.

The clutch plate or clutch adjustment seems to be the most likely thing in that it is not disengaging fully. Check the adjustment. There should be about 1" play at the top of the pedal movement and then the clutch should start releasing about halfway down. The other thing it could be is worn gear linkages and joint bushes. Have someone move the gear lever and check for play along the gear change train from the gear lever to the gearbox selector input.

Rock the bike backwards and forwards while trying to shift the gears. If the lever moves up and down but the transmission does not shift, the shifter shaft in the transmission may be broken. When doing this test, make sure the final drive chain is on the bike.

Good Luck
Steve

More than likely the shifter pawl has broken. Breaking in 5th gear is kind of unusual however, they usually break between first and second.

You'll have to remove the outer primary cover to look at the shifter pawl. It's partially covered by the clutch assembly.

Tighten clutch cable until the car would start to move when the clutch peddle is 50% depressed, Before you do that, with the clutch fully depressed and in 2nd gear, start the car and slowly let off the clutch. You may find that the clutch has to be released virtually all the way before the car moves. It should be at about that 50% I spoke about

Have the diagnosis performed by certified transmission shop. Possibly bad solenoid in transmission.

it probably needs a clutch adjustment. try rocking it hard up,down side to side while changing gears. some peopl ecall it transmission lock.