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Jeff, From an engineering standpoint, the wrap around tin is the better cooling option for air cooled engines. Forcing the air to flow around the back side of the cylinder and add more flow across the fins near the exhaust port reduces cylinder temperatures. NACA (forerunner to NASA)figured that one...

A bit of quick info on belts, the reason IH listed the belts as 3/8" is because that is the "running" width. Or, where most of the energy/power is applied and transferred through the belt. Not the actual outside dimensions. Good info here: http://www.gizmology.net/pulleysbelts.htm

Is it sad that my only thought is "I wonder how much they would ask for those fenders?"