If you are going to drop the rig anyway (which is fine, not much sailing on the ICW
anyway and no worries about bridges), why not just buy a power boat
? Much more practical on the ICW
than an underpowered sail boat.
Also, why transport. Complete a leg and stow it there. Return later for the next leg minus the long cross country tow.
Get a copy of "The Waterway Guide". Specifically about the ICW.
The ICW runs (non-contiguously) from Texas
to NJ so yes you could do this for a long time....then there is the Great Loop.