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Heat should do it. You could try to start with a good heat gun and if that doesn't work a little propane with a pencil tip. Map gas might be too hot. Just be gentle with the pliers.
I tried a seal without silicone and it leaked right away.
Now got the other single lip with high temp grease on both sides of the lip and silicone on the outer edge.
I was able to push the seal most of the way in with my thumbs since the bike hadn't cooled all the way.
The crank is wider in toward the bike like it bellows or the opposite of a bevel. A design to ensure the seal works? The lip of the seal is against the surface of the metal around the shaft and on the back edge.
The sleeve had conformed to this shape reflecting and has a groove from the seal.
I believe this means the seal needs to be as far in as possible to seat right.
However, that seal would work if you pulled the engine & split the cases. The head would have to point down onto a work bench and try to remove the lower case. The crank would then have to be lifted slightly in order to slip the stock seal on (both sides). Might require unbolting the connecting rods for clearance. I did this once to a Honda Nighthawk motor to replace the alternator chain. Pulling the XS11 motor out is really not that difficult. I have done a few. Maybe it's time to fix it correctly the hard way.
I was talking to a mechanic friend about the difference between viton and buna rubber seals for the crankshaft. His opinion is buna is better for this and that's the one Phil has working. I got 500 mi with a dry foot with the viton seal but if needed, the buna is a better replacement.
The original split case may not work if the seal sat on a shelf for 30 yrs- one on ebay had a manufacture date of 1987.
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