(she insists it was every year).

At roughly $14 each times 5 units gives $75 which seems like a waste

This, combined with the other posts, starts shedding light on the wife's
perspective.

As an aside, as a boat owner and a spouse, if all it costs if $75 to allay
the wife's fears then THAT'S GETTING OFF CHEAP.

If she's not "getting the hang of" sailing, but is paying attention to
safety stuff like this then I'd wonder about how comfortable she is on the
boat AT ALL. Some folks just do not take well to being on the water.
Those that like being on the water often fail to notice this. Raise the
possibility of your wife taking sailing lessons, with one of HER OWN
friends, not you and not with the daughters.

Nobody likes to make mistakes in front of people they know. Learning to do
something often means admitting there are parts of doing something that you
didn't understand or have been doing wrong. Making those admissions in
front of someone you're PAYING to help you is quite a lot easier than doing
it in front of friends or family. But unless there's an open and unbiased
atmosphere for learning then, well, no learning will happen.

That and I've also heard plenty of stories where one spouse, upon taking
lessons, learns just how many mistakes the other has been making over the
years. It's a double-edged sword. Be prepared to be humble as she
out-sails you. Then YOU get to sit back and relax as the passenger!

-Bill Kearney