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I was able to drop the ?33-35' deck stepped mast on my boat at the dock and bring it home with a dinghy trailor-not a walk in the park, but once home, reinstalling new standing rigging on the mast was a breeze.
I went with a local swaging company, Seattle area, for simplicity.
But if I had to do it again, unless I was replacing only one shroud, (which unfortunately I do have to do since I bent a stud when it caught in the companionway as we were cranking the mast back to vertical again), I would bring the mast down.
It would probably even be worth the cost of crane time, and even so it sounds like you would save $ compared to hiring a rigger.