Trucking is less wear and tear considering you don't have a flybridge that has to come off. However, Chicago to NYC is a beautiful trip.....mainly the Detroit River and the entire Erie canal and Hudson River and one of my favorite trips.
The problem you'll have with trucking is that the trailers are all made for shafts and if you have a Sovran 43 with pods then the boat has to sit higher and you start running into height restrictions etc. I just went through all this in considering the best way to get a Sovran 43 from CT to Key West. Happy to provide further detail.
True enough, along with the cost of removal and re-install/alignment etc... The same "solution" applies to removing all the hard top fixtures to bring the height down. In the end, transporting on her own bottom was the more economical and simpler option.