I have installed hydraulic steering on several boats with short jackplates and there has always been an issues with the fittings hitting the transom. So as Steve mentioned raise the motor on the plate mount itself go with greater setback or as Iam doing on my 492v go with a hydraulic plate. Then you can just raise it and trim motor up. I ran other boats just being real, real careful and remembering not to trim to high and snap off fittings.
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