1) Do I need the transom saver for this size motor? If so do I keep it on during travel only or when not in use? It depends, is the prop and lower unit/skeg well above the ground when on the trailer? You can put it in Neutral and reduce bounce with a bunji cord. Otherwise a transom saver would be advised.
2) when I am they for the day do I shit off fuel supply and let it pull carb dry? You say below it will be run 12 months per year so if you run Stabil or Starton, both combined with Seafoam, no reason to run the carb dry between outings.
3) I will fish every month of the year. So do I do anything extra for winter? No. If however you plan to let it sit for 3 months then I would run it dry and fog the cylinders by pulling the plugs and using fogging oil and pulling the starter cord a few times to lube the rings and cylinder walls.
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