question for those who know how to sail
Sailing either a small daysailor or a larger cruiser each requires their own set of skills. Daysailers can be manhandled and tend to provide more response to sail trim and weight distribution. They require better boathandling skills under sail since they don''t have an engine for docking.
Bigger boats require more forethought and judgement. They often require greater physical strength. If something goes seriously wrong someone is more likely to get hurt and the damage is bound to be greater.