Not a nightmare at all Wob. If you let the squish band follow the dome of a piston with a timing edge radius and you center the head insert in the cylinder bore, as would be good practice with a non-radiused piston, you will end up with a thin, sharp, vulnerable edge on the insert that is susceptible to overheating and detonation.
But the solution could not be simpler: do not center the head insert in the cylinder bore, but around a collar on the cylinder.
You could also center the head insert in a larger-diameter part of the cylinder, like this:
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