As Freesail has pointed out, height is going to be a problem. Most highways will have a clearance of 14' or so, but anything higher is going to be a problem.
What boat are you trying to move. I think going with the second solution is probably better, but it will be more expensive. However, I don't think it is all that feasible, given the height problems.
Given a draft of five feet, I would guess that the boat's height is going to be at least 10' from the top of the pulpit railings to the bottom of the keel. Add another two feet for the cradle and then another foot for the trailer and you're up to 15'. That will probably be a problem. Although you can probably clear many highway overpasses, local ones will probably be lower.
Try giving Brownell Systems a call. They may be able to move the boat using a large hydraulic lift trailer, which would allow them to lower the boat onto blocks and stands without the need for a crane. They're located in Mattapoisett massachusetts.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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