I am seriously considering a Helmsman 38 pilothouse and as I tend to single hand my boats most of the time would like to hear from others who have one and single hand it. Any problems or suggestions would be greatly appreciated. Also looking for one in the 208-2020 age in the PNW.
I think the truthful answer is,
it depends.
Seriously though, comfort single-handing a boat depends on many things. Mostly the operator's experience, what kinds of boats you've been comfortable single-handing in the past.
It also depends on how you will use the boat. Keeping a boat on a mooring and rarely docking is different from frequently threading your way down tight fairways into narrow slip spaces.
The boat certainly makes a difference with some styles and sizes being easier to single-hand than others, but this might be secondary to experience and use.
The answer is different for everyone. Some people are comfortable single-handing a 60 footer on a global circumnavigation or in any busy harbor. Others won't go out alone in a 15 ft runabout.
Though I usually go out with the Admiral I effectively single-hand most of the time. For me and my usage, I've found that having easy, safe access to all points of the boat with protected, full walk-around decks has become an absolute must-have.
For my usage and waters, I've often found myself in tight docking situations, not much room to maneuver between hard damaging things (rocks and pilings) and expensive things (other people's boats) with adverse winds and currents tossing me around. Being able to quickly, easily, and safely get to any part of the boat to fend off, hang a fender, tend a line, in any weather or sea state, is critically important to me. I'm well past the age where I can safely (or sanely) do the 'clinging' dance moves precariously balancing on a narrow unprotected shelf of a deck the width of my shoe. Those younger and more limber have different priorities.
While I prefer the look and visibility of a raised pilothouse (and have owned a couple), I recently bought a Helmsman 38 Sedan for its full side decks, protected by bulwarks and not just railings, which for me and my use makes a
huge difference in being able to comfortably single-hand.
Your mileage may vary.