Solo sailing, as most of us have found, is actually easier on a well-equipped larger sailboat than a 23-foot trailer sailor. I move up to a C36 years ago, and tripled by solo sails because it had: autopilot that acted as a (stupid) extra hand at the wheel, good winches to multiply muscle power, comforts (head, cup holders, fridge, etc.), stability so I did not fear getting into weather, push-button diesel engine that would bail me out. Chatted with a buddy with a C45 who stepped up through the Catalina line 5 foot at a time, and he told me the same thing - sailing his boat was much easier than when he had the same model as mine.