If you have a perko or some other design similar, a spring has to seal the side of the perko that is the normal pickup point of the boat. If this does not happen, then more air will be sucked in than water. In other words, air is being pulled in the normal water intake under the boat. Put a piece of duct tape over the hole and try it again on the trailer. If it works, then that is your problem and make sure to take the tape off before you go out.
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