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Seems to me that the generator cannot handle the startup amperage for the air conditioner. Could be the breaker on the generator is faulty, the stated startup watts (4000) for the generator are overstated or there is a fault with the generator.
Try the generator on another trailer if possible and see if it starts that air conditioner.
Try another generator if you can get access to one.
I might try a hard start kit on your son's trailer. It's only about $20 and can be installed DIY in less than an hour. Lots if video's on YouTube.
Stuart
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