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What should I be aware of when replacing the head gaskets on the front and rear cylinders on a 1988 Honda Shadow VT600C? ie. tightening bolts, replacing o-rings, order of reassembly, things to look for, compression test, etc.

I'm hoping you have a proper repair manual for the bike - 'cause that's a hefty undertaking you're into. Other than that, I can't help you as I have no experience with these bikes.