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Re: How does a boat break free of its moorings?…
A ten to twenty foot storm surge is not out of the question, which would make your lift pretty meaningless. Also, being on a lift exposes you to the full pressure of any wind, and the lift may not be designed to withstand Cat3 winds, which are also expectable. (Florida is overdue for some big ones.)
So you might want to ask your insurer if they have any thoughts, and then ask the lift maker what they guarantee or advise.
While any lift that is sufficient for your boat will certainly pay off in terms of keeping the bottom clean, if that six month layup is going to be during hurricane season, you might want to look into indoor storage, or yard storage, even if that means a haulout and launch.
Leaving the dockwork at a minimum (four pilings is plenty and your lift apparently works as it is) and paying for better storage might actually be your best investment. You can probably get some folks from the lower USCG Auxiliary or US Power Squadron to come around and take a look, if you want some experienced eyes and opinions for free. The ASCG Aux can also give you a free safety inspection--no penalties if you need anything, just a "here's a list" or a gold star (transom sticker(G) if everything is in good order.