When I resize or "pinch" sleeves I usually determine how tight it needs to be by the condition of the piston and sleeve. If the piston has a mark or scratch in it I will go tighter to get it wear back in.
Most engines in good condition I try to make similar to an engine after a gallon on it. There is no need to pinch it so tight it needs a long break in. I only recommend a couple tanks but it isn't really even necessary. In most cases the pinch will last as long as it did from new or longer.
Rex