Wednesday's Random Slang-o-rama: Sail close to the wind

Those of you who are nautically inclined will no doubt know the origins and meaning of the phrase sail close to the wind, and why it has an air of danger about its definition. However, I do not, and since I'm mucking around with bits of maritime history as I trudge along drafting book #8 of the Silver Rush series, it seemed time to look this one up...
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The American Heritage Dictionary of Idioms by Christine Ammer summarizes as follows:

sail close to the wind: Be on the verge of doing something illegal or improper, as in "She was sailing pretty close to the wind when she called him a liar." This term alludes to the danger incurred when literally sailing too close to (that is, in the direction of) the wind. Its figurative use dates from the first half of the 1800s.

Well, that's pretty cool! And I rather like the sample sentence. There are all kinds of folks my protagonist Inez could accuse of sailing close to the wind in my current work-in-progess. In fact, she could be probably be accused of the same.

There is a little more back'n forth about the phrase over at The Phrase Finder, to wit:

This is a true sailing expression. Sail boats have different characteristics, but all need wind. Some can harvest the wind better than others. If you sail close to the edge of direction that the wind is coming from you may well lose the wind altogether, but you may be able to make better progress than a boat that can't sail as well in such a difficult situation. Thus, if you can 'sail close to the wind' then you can benefit, but you enter a risky area and may lose all!

I looked around a bit more, but that was about all I could find that shed light on this particular phrase. At least, the timing gives me license to let my characters sail close to the wind—in some cases, with disastrous results.

Sailed too close to the wind? Or a reef?...
Shipwreck by Ivan Aivazovsky, 1854