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Ross, how/where did you plan to load the anchor onto the boat? If you are bringing it down a dock, or on a handtruck, maybe you can instead lash it to an empty 55-gallon drum or other float, and just tow it out instead? (One gallon of seawater weighs about 8.5 pounds.) That way you also can't damage your deck or hull bashing it with the anchor.
The rigging should hold it, after all, you main sheet is "carrying" the whole mass of the boat when under sail. Ditto for the hard parts it is attached to, but I'd still suggest tying on a safety line, or a recovery float, in case something lets go.