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Is the far right pulley supposed to ride on the bigger one? Thanks

Is that an OEM belt? Don't usually see a cogged belt as a clutching belt. They usually grab when they engage. Pulley riding on the other pulley shouldn't be a problem as when the tension is off the belt it shoul not be turning the pulleys.

That kind of belt was on it when I bought it. Is there a parts list someplace or do you know what belt it takes?