Going off the track and getting debris in the chain is probably the most common cause for losing a chain and the subsequent damage. If you go off, come in and clean it out right away if you can. Also, make sure the chain isn’t loosening up by the motor sliding back. If the clamps bottom out on the track, and you’re not using an engine stop, the motor can slide backwards easily and you lose the chain and never know why.
Triflow lube is fine for between sessions, but you really need something heavier on the bearing, especially if you’re running a 10T driver, as the bearing usually isn’t a roller or needle type. I like to take it apart and lube the crank where the clutch sits with Triflow grease every day. Then regular Triflow lube between sessions. Don’t get nuts with the stuff though, since it has Teflon in it, you don’t want it flying all over the clutch discs.
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