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Many articles and books I've read suggest checking the pressure in your bike tires every day before starting out in the morning.

How far above or below the Owner's Manual recommended pressure for a cruiser can the pressure be before the pressure should be readjusted to the recommended point?

I can't speak to the other brands, but Kawasaki manuals tend to be very low on their recommendations as to tire pressure. I believe they recommend 36# psi front & rear on their cruisers. After replacing both tires in a very short time due to flat spots on the outer tread, I raised the psi on both tires to 40#psi. I now have over 22000 miles on both tires, most of which are the replacements with the increased pressures