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The boats I have been on with a boom furler always went head to wind to furl...

Furling with wind in the sail is simply a quick route to disaster. You can furl an in-mast system with wind in the sail, but you will quickly overload an electric system. The Hood systems have a really loud annoying overload alarm. You also have to very careful as you release the outhaul or you will get a jam. If you head up, you can furl the sail completely in seconds. In-mast is quicker than a boom furler. As I said above, the down side is the huge performance hit you take.

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