Approaching a mooring into the wind is good advice for ragbags or stinkpots. If you approach with the wind at your stern, you will likely run over the mooring. Most times that just means some scratches on the boat bottom. Been there, done that.
On a windy day, the tricky part with is to get close enough to boat hook the mooring without overshooting and scratching the gel coat. The second tricky part is hooking up the lines before the boat falls off down wind. If your too slow then you're holding the boat against the wind with arm strength. My shoulder stills hurts when I think about this.
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