Transporting Big Boats

The reason for all the adventure and fun of sailing to Fort Lauderdale was to avoid having to truck the boat out of the Keys.  Although we were in a nice full-service yard capable of removing the mast and hoisting the boat onto a trailer, the next part was complicated and expensive.  It would have cost $1200-1600 dollars extra to secure the permits and escorts to move the boat the first 130 miles.  Oversized loads have to move under double escort and then only after 2100.  Once out of the Keys, the load can't be moved at night!  Therefore, at least an extra night on the road or more.
So we sailed to FLL and paid around $900 to Playboy Marine Center to haul, pressure wash, dis-mast, and block TANGO.
That is $900 cold cash.  No Checks.  No Credit Cards.  And no move until paid!  The yard opens at 0700 and closes at 1800.  Closed.  No entry.  Period. But it is a clean, organized, and otherwise friendly place with expert staff.  But they don't have a sanitary pump-out, so either dump it before you get there or plan to transport your waste in the holding tank.
Preparing the boat and mast is not hard.  Go to the local Home Depot with the rental car you used to get to your hotel.  I did mention that you can't stay on your boat, didn't I? Get a roll of bubble wrap, some of the plastic wrap that comes on a roll, some shipping tape, and if you can get it the self-clinging plastic wrap around 12-inches wide that's used to wrap luggage and pallets of boxes.
Picture your stuff in an 85-knot wind bouncing and vibrating on a flat-bed for 1000 miles.  Now pad everything that touches anything else and seal it from road dirt, rain and mud.
When you take the boom off the mast, leave the sail on it with the sail cover still on.  Store it in the cabin sole.  The sail and cover will not only protect the boom, but it will also protect your cabin sole and furniture from the boom.  Put the dodger and bimini frames in the cabin with generous bubble wrap padding and secure them from any movement.  Tape all the drawers shut.  Plastic containers can chafe through their own bottoms if left in cabinets unpadded.  Liquor bottles will break.  My suggestion is to pad them and put in the ice box and sinks.  At least then the fluids will be captured and drained.
Close and dog down tightly all ports and hatches.  If your seals are suspect tape the outside against rain intrusion.  Remove Dorade vents and tape their holes.  Remove all the things that stick up.  Deck-mounted antennae should be removed or laid down and secured thoroughly along their entire length.  Radar masts should be laid down on deck and padded and tied so they cannot shift in a hard stop.  Tape or lock all outside lockers after checking their contents for security.  Check and tie down the batteries.  Dinghies and motors should be removed and if necessary shipped separately.  If you decide to store motor below, drain the tank, ensure the oil cannot leak and secure it heavily.
Drain water tanks and, if possible,  fuel tanks.  If you can't drain them, consider filling them.  The worst situation is half-full.  If the tanks aren't properly baffled, and most aren't, the sheer force of 50 gallons of liquid moving at 60 MPH in a panic stop is enough to tear a tank loose or blow a hose off.  Your sailboat is built for 15 MPH.
Since your rigging has been disconnected, make sure that all the turnbuckles are pinned so they can't vibrate loose and get lost.  Pad them so the don't mar the boat.  Lock down the anchor well and make very sure that any anchor left stowed on rollers or mounts cannot possibly jump off and try to anchor your boat while the trailer is rolling down the road!  Even if it only comes out a little bit, a swinging anchor will destroy the bow.
For your own sanity, don't try to follow your boat down the road.  It's just not good and it is useless.
Unless you own the trucking company, any attempt to "correct" the driving habits of the driver is not going to be a pleasant encounter.  Besides, you hired a great company after getting several recommendations and researching them on the Web, right?
What happens at the other end may be as simple as rolling into a full-service boatyard with all the equipment to handle re-commisioning your boat or as complex as being the first large sailboat on a small lake with only a ramp for your launch.
In the Marines, we make special efforts to "recon" every beach before we get there.  You should do the same for the arrival of your boat.
Can the trucker who drove it there get his trailer wet?  Is it even possible to launch on the ramp you've chosen?  Take the draft of your boat, add the height of the bottom of the keel on the trailer and you have the minimum depth of water needed to launch.  A typical 6-foot draft with an added 18-inches of trailer will need 7 and a half feet of water to float off, minimum.  Is the ramp long enough to allow the back wheels of the trailer to remain on solid concrete with the center of the boat that deep?
Man-made lakes are variable.  The dam operator can raise or lower the levels and therefore the depth at the ramp.  In planning the move, be sure to check that level and the ramp.
Check the availability and capability of the crane or lift that will set your mast.  Setting the mast with a capable, professional crane service is a snap compared to the process necessary to use a fixed lift such as a gin pole.
Man (or woman) power is needed.  I had 13 people on-site for my last launch and none of them felt unwanted.  Hold a good safety brief, explain the entire procedure, assign jobs and expect to move from area to area checking on progress.  Bring enough food and water to keep them happy.  Beer is for lunch afterwards.
Finally, make sure everything is there tools, hardware and people to do the whole job as efficiently as possible.  Ask the driver to plan on being at your launch all day.  If the driver only scheduled an hour to get your boat off his trailer, he is not going to be happy.  Remember this could be his first time!  Ask him not to schedule a pick-up on the same day.  Have plenty of hardware and supplies.  Don't let the job stop while somebody runs to a store for sealant.
Have a backup plan.  If the mast can't be put up because of a breakage or lost parts, can you launch the hull and raise the mast later?  If the boat leaks when you back in the water, can you fix it?  On and on forever!  You can't anticipate all of them, but at least the most probable "fails" can be worked out.
Absolutely last is to make sure you know what form of payment the crane operator and driver need.  Your credit card may not work on-site and they may refuse a check.  Everybody seems to like cash!