Good trucking seems best
Your story is sad/amusing. I had Asylum trucked from IL to CT, no choice, and the trucking firm did a great job. The rerigging in CT had a few wrinkles that I had to iron out over time but I was very pleased.
After I got my Masters License, I did some deliveries and associated with others guys who did. Seems to me there are a lot more risks with a water delivery. There are many good captains but the schedule is always tight and we all know that schedule should not win over the weather, but it does. There are also some not-so-good captains out there and it is hard to tell without a lot of due diligence.
The best delivery I ever did was my own boat when I moved it from CT to NC. I took my time and had a great time. When I realized there was little money and no fun in meeting a tight schedule, I stopped doing deliveries.