Sounded like Carroll really wanted that extra week for Denis to recover that an Apr 5 start affords. Shipping around not mentioned as a concern.
If current plans are still on schedule, Denis is either en route or arrived at Churchill. From there, it appears Carroll will watch the weather channel and ship to New York (or Chicago if Aqueduct is shaping up to be sloppy).
I do have to agree with you and wonder if Carroll is over-analyzing all of this, with the path through the Ark Derby looking less taxing overall. In addition, I think the Ark Derby offers more money than the Wood.