If the shocks are worn out, get off the machine and lift up on the back rack. This takes up the slop between the shifter box and the transmission, and usually allows me to shift. I also had an issue with the thin steel plate behind the shifter box. Got a crack in the top , so it was flexing, creating more slop. Welded it shut, good as new.
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Make sure the spring on the brake pedal that operated the park interlock hasn't stretched or come off the interlock, If the interlock and spring are ok,the problem most likely is behind the gear selector cover on the transmission. Water,moisture can get into this area and corrode the shift gears up or possible you could have broken tooth on one of the small gears
From experience, its one of two things, bent or worn out shift forks or worn out engagement dogs on the gears themselves. A professional job. Does it fall out if you hold the gear shift up or down while driving? Take it to your local professional!!
There is a kick start gear that goes on them often if not kicked properly all the time. ., pull case check for damage ( metal chips flakes broken gears teeth ext ext ) see if that's it ., dose it shift through the gears dose it run if pop started , careful starting it as if it's running and there is damaged kick start gears that could cause a lot more damage...?.