We went from a 25' Albin to a 32' Ennos Sapphire and are now in a 42' Nordic Tug. As has been mentioned, the biggest challenge generally is docking or undocking.
It has been my experience that the larger the vessel, the easier the docking. Larger boats tend to track straighter and stay where you put them (more or less). Everything happens slower (if you let it) and winds and currents usually have less impact while you are maneuvering.
Campbell River BC