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I've never seen a seeping base gasket constitute a thought to stroke the motor..... fix the leak and ride on unless your looking for confirmation to do what you want...
Seems like a good idea to me!!!
He will have 90% of the work done anyway so why not just go that extra 10%?
If you've got rocker box leaks let us know. Get it out at 70 mph and run it for a few (10 or so) miles. Check for leaks. Report back. You need to let it warm up a bit before beating on it. Cylinder base gaskets are a typical HD repair job where ya gotta pull off a lot of good parts to get to the bad ones.
I suspect a leaking stator plug. I have a saying: "show me an Evo motor, and I'll show you a leaking stator plug."
FWIW, the stator plug design was inherited from the Shovelhead, which ran a "dry" clutch with just a drip feed to oil the primary chain. It was never meant to live in a "wet" primary and keep all that oil inside. The motor company has redesigned the plug at least three times and each one leaks worse than the one before it.
What I'd do is clean up all that crud around the motor then sprinkle talc on that area and go for a ride. Watch where the oil appears first. Remember, wind can move oil to places you'd never imagine. I was convinced I had an oil leak between the cases a couple of years back because the rear motor mount, behind the motor, was soaked with oil. Turned out the oil was coming from a leaking fork seal!
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