1998RM250 said:
The actual kickstarter itself where it pivots has been worn and the kicker has been wearing into the works connection frame guards, but I dont see how that would effect it coming off... The bolt is removed and I can actually slide the kickstart back and forth a few mm on the shaft, but then it's like it hits something and wont go any further. Didn't see any flakes in the oil, but it feels like its stripped and skipping when I kick it now!
Your kickshaft has a gear that can break teeth off, which isn't uncommon. I've seen it on plenty of thumpers, not so often on smokers although I have been witness to it. I've noticed people that "whiskey kick" their bikes, just kicking and kicking without first bringing the piston to top dead center through the compression stroke it impacts that gear a little too much and teeth begin to break off. It's a fairly easy fix, but often you have to buy the whole assembly and replace it completely.
Okay, here's the diagram of your kickstarter assembly, that is if your bike is the same as your name (98 rm250). The gear is the part #6.
If it's skipping/catching, skipping/catching like you said, that would lead me to believe that this is your problem. If it were an issue with your kickstarter being stripped out then it would twist on the kickstarter shaft all the time and wouldn't ever really catch, it would just continue to pivot. A few teeth being broken off the kickstarter gear would give you the issue of slipping then catching all of a sudden because it's just like having teeth broken off your primary sprocket. Your chain skips and catches and eventually begins breaking more and more teeth off the sprocket, this is the same that happens to your kickstarter gear so it will only continue to get worse. Not only that, but you're dropping more and more pieces of metal into your bottom end, so after changing out the gear it would be a good idea to flush out your bottom end fairly well before deciding to go ride again...