The AI appears to lack any ability to account for the vehicle under it's helicopter pulling on it. This hilariously makes the AI pilot glitch out and he goes around in circles and occasionally flys over the object hes trying to pick up (tested with hunter). On the first attempt to get this to happen again, the AI took approximate 7 circles before he picked up the hunter at airstation mike 26,he then flew to Stratis airbase, where he did some crazy stunts (going in circles, almost flipping the helicopter upside down multiple times) another 22 times before he finally dropped the vehicle.
In the video linked below, was my second attempt to get this to happen again, but this time the AI wasn't as abysmal with its piloting, this is still pretty brutal regardless.