It totally depends on the individual and your flying skills and your
instructor's experience and ability to convey the essential information
about the aircraft you are transitioning to.
I transitioned from a C172 to a C182 without difficulty as soon as I
met my club's minimum flight hours experience.
Last month, two members of my club damaged both the club's C182's.
They are partners in owning one of them. Both were damaged in cross
wind landings. Neither incident was reported to the FAA nor NTSB,
despite causing sufficient damage to both aircraft to be a reportable
incident.
Insurance did not cover the partner flying the aircraft they owned (I
was told the reason but cannot remember), but the partner flying the
rental aircraft was covered.