
The stated purpose of Instructor Weekend Off is to "get away" from all those annoying general club members, i.e. the ones who pay to take lessons. Former Head of Instruction Jim Rogers put it this way: "The club may disintegrate without us, but we'll only be gone for a few days."
The private event helps to facilitate "bonding" among sailing instructors--who are better, harder-working people than all those annoying general club members--and to let the instruction staff have a big party weekend at general club members' expense. It's a reward for doing all that "work" teaching lessons (as if teaching sailing is actual work), organizing Commodore's Cup, and so on. Except, instructors are already getting paid by the hour and the commodore gets paid a stipend.
The sad fact is, when you join the Hoofer sailing "club" as a paying member, club leaders are mainly after your money which will help make life more fun for them. There are many other instructor-and-BOC-only events during the season, including weekly instructor-only parties every Tuesday night (not open to general club members... sorry.) Yet, those sailing instructors weren't "hired" because they were qualified; they got hired because their party buddies were on the hiring committee.
The problem with a few club members (e.g. instructors and BOC) having fun at everyobody else's expense is that it is anathema to a true, egalitarian club. Exclusiveness is malignancy in a social organization like Hoofers.