I went from a 22 to a 33 and single handed both of them. I thought the 33 was easier because it didn't react as quickly to changes in sail shape and allowed you to slow things down a bit and recover from tacking the boat and trim the sails without laying the boat over. If the boat is laid out correctly for single handing then you will have no issues and actually be a bit more relaxed. Docking will always be more difficult with a larger boat simply due to the inertia of a heaver boat. Anchoring will be the same.
2007 Hunter 49