Make sure your mounting screws are torqued equally. If one screw or bolt is over tightened it can cause issues and not allow it to lock.
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Does it have a air shock on it that may have went bad?
Sounds like he has a powerdrive/terrova and it’s hard to slide the shaft through the steering motor.
Mine can be. It’s easier to slide if I lift straight up about half way to get the weight off the shaft and more balanced them lay it down and slide it back and I lay the head down. Also pull a string tight with it deployed on the trailer and make sure shaft is straight. It could be slightly bowed from rough trailer and boat rides with head unsupported. I made a diy support from a rod holder base all-thread rod and a piece a metal.
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I drive mine up. Hit the release, hit the go button and catch it when it comes up.