boom as crane
I recently heard of a setup which called for the boom to be attached vertically with a pin at the clew end to the taff rail, lashed to the stern rail and extending upwards several more feet with the boom vang acting as the lifting mechanism at the gooseneck (top) end for the mast. This lifted the mast to about a 30 degree angle so that the base could be engaged in the tabernacle. The jib halyard attached to the stemhead, and the tail run back to a winch provided the rest of the pulling power to get the mast upright, and the second pin engaged, and finally the forestay. All the shrouds and backstay are connected prior to the mast raising. Hope this spurs some further thoughts on how to raise that ugly stick to upright!