The gear shift on smaller outboards is typically a stubby little 3-inch lever tucked away on the starboard side. On a tender or skiff, it’s easy enough to reach around and shift. You helm the boat from starboard and it’s right in front of you. But on many trailer sailers, you helm from port because the reach across the cockpit is too great from starboard. You must reach through, around, or over the stern rail. The outboard may also be considerably below your seating position. All of this may not be too bad when backing out of the slip, but when returning, shifting into reverse at just the right moment, and then back into neutral, it can be a challenge.
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