Sorry in advance, Ishmael, but for all of you newbies out there - this is e-ZACTly the reason why you don't buy or build custom boats. This is one of the huge hurdles to be faced.
And $75K of receipts for improvements to a custom boat does NOT equal $75K in value, unfortunately, Ishmael. It's a false equivalency.
With insurance companies, it all comes down to assessment of risk. For every question you answered "not applicable" - the trailering, for example - it captures another parameter that is crossed off the Insurance company's coverage.
So, for instance, at some point during your trip to
Florida, you suddenly decided you needed to
trailer the boat for a portion of the
route - because you have already checked off "N/A" on the trailering, you would NOT be covered in the event you chose to
trailer the boat.
This is the Insurance Company's way of getting all elements and contingencies into their records, so they will know what claims down the road they will accept or decline.
Their reasoning around the precise dates is the same:
hurricane season has start and end dates in Florida; they want your trip dates to be outside of
hurricane season. Again, if you provide trip dates that fall outside of hurricane season, and then the dates you actually travel change, and happen to fall
inside hurricane season, you would not be covered.
This is increasingly the case for all cruisers/sailors/boaters. Named storms are becoming more frequent and more violent. Many people are getting into
boating with little
training or understanding. This is the insurance industry's response. (Source: Association of
Marine Industries Conference, January 2020)
Best of luck for your trip - and on getting your insurance,
Warmly,
LittleWing77