Unsure of visa-exempt extension

Hey, been starting my research on my trip in Oct and want to stay for a bit longer than 30 days. Im visa exempt (US) and am planning on getting an extension while there. What im unsure of, is whether my outward ticket will be okay being passed the 30 day mark or is it necessary to be within the initial 30 days?

Also, would it be better to just go on a border run rather than extending? Trying to minimize the risk of messing anything up and ensure that my trip goes smoothly.

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