You turning it into the boat the wrong way (possibly)? Sounds dumb but it will only tun into the boat counter clockwise. You will not be able to get the downward motion due to the handle not allowing you to push down on it to allow the skeg or shaft to clear the corner of the boat.
Problem #2 - low transom with 20" side boat - side of the boat are considerably taller than the transom. SOL or unless you can some how make a transom saver for an outboard motor work on the old long-tail.
Solution to above problem - ratchet strap the motor handle down in the bottom of boat to where the motor cannot bounce.
Life ain't easy and dry bread ain't greasy.
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