I could strongly argue to get a training captain and make the deliver a training event. A good capt should know the waters and issues with that run.
And, if you haven't done that run in a power boat, there's many places that have their issues. I've had several "issue" places in my Mainship 400. Chesapeake Bay is big enough for issues, Dismal Swamp, Abermerle Inlet, Catherines Inlet, Neuse River, Hell Gate, Little Mud River, Jekyll island, Daytona Beach, Lake Okeechobee and the canal. Nothing impossible, mostly current, tide or wave issues, but something to be aware about and plan accordingly. I've only done it once, so I'll let the most experience comment