Mike We've pulled a lot of masts at clubs I've been at, and
find it"s not too hard to do between two boats with Spinnaker Halyards (that is if you do it while the boat is still in the water). It's harder to do if you have double or triple spreaders, but single spreaders are normally slightly above the mast center of gravity. If you think the spreaders are close to the CG, add a little bit of weight to the base of the mast. It just requires a rope loop (with a retrieving line) pulled up by the two lifting halyards to the spreaders (or below the lower shrouds if you have to and a control line at the base of the mast. Both lifting boats will heel inboard a little, so it's better if you can take another halyard outboard from each boat to something like a dock or even to the deck of another boat to minimize the heel. The weight is well within the capacity of two halyards with winches, you just have to coordinate it and proceed slowly. You take a strain slowly and just enough to hold the mast before you disconnect the rigging, but you don't take enough strain to jerk the mast up and out of control. If the mast is through deck, your lift has to be a little higher, but the CG is going to be lower.Any way, if you saw it done once, you would realize it's not too difficult, but it's something that should be done with care. The boatyard next my club no longer handles masts because they got burned with liability issues, and I have seen the results of some boatyard incompetence in mangling the headfoils of furlers, but I believe most yards are competent.BTW, most truckers travel the mast alongside the boat on the trailer rather than over the deck, so the mast should be wrapped to protect it and any halyards you leave on it, Also wrap inside (between the wire and the mast) of any rigging or wire you leave on, because it will vibrate and gouge or mark your mast.Good luck whichever way you decide to go. - Joe