I have a new appreciation for my small boat. I can easily catch my shrimp pots at the stern after nosing up onto them on the starboard side, easily step out the pilot house door to catch a cleat at the dock, easily step out the pilot house door to raise or drop my anchor, and see my fishing rods from my helm while trolling.
I had never thought about how hard it would be to have to run from a helm station to catch my pot buoys or not being able to see my fishing rods from the helm. I am six steps from the helm to the cockpit or anchor, and two steps from the helm to the dock to tie off. I can see my bow pulpit and my cockpit by turning my head.
I think "handling" your boat single handing is more an issue what activities you plan than if you can dock it by yourself. Some activities limit themselves by needing to have both an operator and a person performing a function to complete the task. I think that is especially true on larger boats.
Even in my small boat, sometimes I stay out until the weather is better to avoid getting in over my head. Leaving the dock has always been easy, but sometimes getting back to it not so much...