Biggest boat for 1 1/2 persons to operate

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In our case we have to take an able bodied seaman, aka one of our adult children and family, because age and mobility are issues. I’ve single haded our 38 in the past even though I use a walker. However the Admiral forbids me from the foredeck and single handling. At the same time, she’s not comfortable stepping off or on the boat with a line after having two hips rebuilt. When we were looking for our grandma-grandpa boat, layout was a prime concern. Flush decks, cockpit flush deck, Sunbridge, most trawler configurations and custom boats were all out. We looked at a 45’ pilot house and the admiral said “too big”. We had thought the Bayliner 38 would be a good fit except for the ladder going to the command bridge. One day I was looking at some pictures and figured out how to make the ladder close to the pitch of a step ladder without it being a huge impact to the port laz hatch or cockpit, and we went on the hunt. The modifications to the ladder worked and we have been enjoying the boat since 2016.
Communications can be a challenge, so we bought some wireless headsets and we are comfortable with the layout and space the 38 provides. I’d like to add a set of engine controls in the cockpit and thrusters, but they are a ways down the never ending list.
My opinion is you should look for a boat that you immediately feel comfortable on. That includes all of the logistics of loading, maintenance, visibility, entertaining and maneuvering.
 
Comfort Factor

I think that it totally depends on what you plan on using the boat for. Are you going to live aboard or just sail weekends with a few longer vacations of a few weeks. Local cruising or world travel, for world travel purchase a sailboat not a trawler. You can cruise around on any size boat, (just sit in an anchorage and look around), the answer is how comfortable do you want to be.
No matter which size of boat you happen to choose the key is to get to know your vessel and practice, practice, practice. As a pilot you already know the importance of building up hours and how many landings and takeoffs in different conditions adds to your knowledge. I have found that the larger the vessel the easier it is to handle.

Happy Adventures
 
Thanks to all for the replies. I've been out of pocket for a week and just now catching up. We really appreciate the input from all of you.

If some of you have more comments then please keep posting. We take all of your comments seriously and with gratitude.
 
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