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Military planes and ground vehicles at army bases will respawn once Rico is out of sight, or after a short time.
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Planes at airstrips should respawn, at least by the time another plane at another airstrip has been used, although more information is needed about the exact spawning requirements. The vehicles that spawn at safehouses will respawn when the game is reloaded, enabling the player to put a spare ground vehicle in the safehouse garage, but vehicles that spawn elsewhere, for example, airplanes at airstrips, do not.
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