Bad question. Instead of seeing duration as a dictate of the low season, think of flexibility and special offers.
It is neither one nor the other: the link between a limited-duration trip and the low season is not a fatality; it is ignoring the reality of promotions and local tricks.
Here, we do not say "two weeks = low season," but rather "two weeks = where can I find the best deal?".
A clever traveler could find affordable plane tickets to Okinawa in summer, by booking early or taking advantage of a cancellation, without the duration imposing a off-season period.
It is a matter of strategy, not constraint.