Consider low profile above water to be a single hander's advantage over one tall and proud but with lots of windage. A huge keel and lots of windage present a hazard to docking. I believe you'll find docking the largest challenge other than sudden changes in conditions. Another advantage would be more sails, only smaller ones. For example, I sailed a 31' Alden Gaff-rigged Yawl, Cutter rigged on the bowsprit with roller furling, and a small marconi aft. The Main had 3 reef points, so with 4 sails it lent itself to single handing even in a stiff breeze. I found the full keel a bit unmanageable back at the dock when the currents were ripping.
Of course if you have lots of technology you can stretch your limits and you may enjoy this video: